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Water → (2S)-methyl 2-(7-(4-allyl-5-chloro-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-2-(3'-(allyloxy)-[1,1'-biphenyl]-3-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate

HRID 1400696
Notes
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Reaction equation

HRID 1400696 reaction equation
[CH2:1]([N:4]1[CH2:9][CH2:8][O:7][C:6]2[CH:10]=[CH:11][C:12]([C:15]3[N:20]4[N:21]=[C:22]([C:24]5[CH:25]=[C:26]([C:30]6[CH:35]=[CH:34][CH:33]=[C:32]([OH:36])[CH:31]=6)[CH:27]=[CH:28][CH:29]=5)[CH:23]=[C:19]4[N:18]=[C:17]([CH3:37])[C:16]=3[C@H:38]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])[C:39]([O:41][CH3:42])=[O:40])=[C:13]([Cl:14])[C:5]1=2)[CH:2]=[CH2:3].C([O-])([O-])=O.[K+].[K+].Br[CH2:55][CH:56]=[CH2:57].O>CN(C=O)C>[CH2:1]([N:4]1[CH2:9][CH2:8][O:7][C:6]2[CH:10]=[CH:11][C:12]([C:15]3[N:20]4[N:21]=[C:22]([C:24]5[CH:25]=[C:26]([C:30]6[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH2:57][CH:56]=[CH2:55])[CH:31]=6)[CH:27]=[CH:28][CH:29]=5)[CH:23]=[C:19]4[N:18]=[C:17]([CH3:37])[C:16]=3[C@H:38]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])[C:39]([O:41][CH3:42])=[O:40])=[C:13]([Cl:14])[C:5]1=2)[CH:2]=[CH2:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 86710748(2S)-methyl 2-(7-(4-allyl-5-chloro-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-2-(3'-hydroxy-[1,1'-biphenyl]-3-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate

Product 1

HCID 86710747
(2S)-methyl 2-(7-(4-allyl-5-chloro-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-2-(3'-(allyloxy)-[1,1'-biphenyl]-3-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate
Yield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (2S)-methyl 2-(7-(4-allyl-5-chloro-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-2-(3′-hydroxy-[1,1′-biphenyl]-3-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (90 mg, 0.138 mmol) in DMF (2 mL) was added K2CO3 (38.1 mg, 0.276 mmol) followed by 3-bromoprop-1-ene (0.017 mL, 0.207 mmol) and the resulting mixture was heated at 50° C. for 16 h. After cooling to room temperature, water was added and the mixture was extracted with ether (50 mL), washed with brine, dried (Na2SO4), filtered and concentrated. Crude was then purified by biotage (5-30% EtOAc/hexane) to afford (2S)-methyl 2-(7-(4-allyl-5-chloro-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-2-(3′-(allyloxy)-[1,1′-biphenyl]-3-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (40 mg, 0.058 mmol, 41.9% yield) as white solid. 28 mg of starting material was also recovered. 1H NMR (500 MHz, CDCl3) δ: 8.05 (t, J=1.6 Hz, 1H), 7.84 (dt, J=7.7, 1.4 Hz, 1H), 7.57-7.53 (m, 1H), 7.45 (t, J=7.6 Hz, 1H), 7.37 (t, J=7.9 Hz, 1H), 7.23-7.20 (m, 1H), 7.19-7.16 (m, 1H), 7.03-6.97 (m, 2H), 6.96-6.92 (m, 2H), 6.17-6.00 (m, 2H), 5.50-5.44 (m, 1H), 5.39-5.29 (m, 3H), 5.25 (dd, J=10.2, 1.6 Hz, 1H), 5.09 (s, 1H), 4.62 (dt, J=5.3, 1.4 Hz, 2H), 4.27 (t, J=4.4 Hz, 2H), 3.67 (s, 3H), 3.27-3.17 (m, 2H), 2.86 (s, 3H), 1.19 (s, 9H). LCMS (M+H)=693.4.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted with ether (50 mL)
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customCrude was then purified by biotage (5-30% EtOAc/hexane)

Sources & evidence

ORD record
ord-a877b0a4d0ea403cabcc505aa154cf23
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08906929B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes