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1,2-Dichloroethane → HCID 68703969, compound

HRID 1619223
Notes
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Reaction equation

HRID 1619223 reaction equation
C(O[C:6]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][N:11]([C:16]1[N:21]=[CH:20][CH:19]=[CH:18][N:17]=1)[CH2:12]2)=[O:7])(C)(C)C.FC(F)(F)C1[CH:25]=[C:26]([C:30]2[CH:35]=[CH:34][C:33](C(O)=O)=[CH:32][CH:31]=2)[CH:27]=CC=1.[CH2:41](Cl)[CH2:42]Cl.[CH:45]1[CH:46]=CC2N(O)N=N[C:49]=2[CH:50]=1.Cl.O1CCOC[CH2:57]1>O.CCOC(C)=O>[C:26]([C:30]1[CH:31]=[C:32]([C:42]2[CH:41]=[CH:49][C:50]([C:6]([N:8]3[CH:9]4[CH2:15][CH2:14][CH:13]3[CH2:12][N:11]([C:16]3[N:17]=[CH:18][CH:19]=[CH:20][N:21]=3)[CH2:10]4)=[O:7])=[CH:45][CH:46]=2)[CH:33]=[CH:34][CH:35]=1)([CH3:25])([CH3:27])[CH3:57]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 27827173'-(Trifluoromethyl)[1,1'-biphenyl]-4-carboxylic acidHCID 204431481,4-Dioxane hydrochlorideHCID 68700570HCID 68700570, compound

Product 1

HCID 68703969HCID 68703969, compound
Yield 32%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-pyrimidin-2-yl-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (64 mg, 0.22 mmol) in HCl/dioxane was stirred for 5 hours at room temperature. The resulting solution was concentrated, and the residue was dissolved in CH2Cl2 (5 mL) and added to a solution of 3′-trifluoromethyl-biphenyl-4-carboxylic acid (117 mg, 0.44 mmol), EDC (85 mg, 0.44 mmol), HOBt (60 mg, 0.44 mol) and TEA (0.1 mL, 0.71 mmol). After stirring overnight, the mixture was treated with EtOAc (50 mL) and water (15 mL). The organic phase was washed with brine (5 mL), dried (MgSO4), filtered, and concentrated under reduced pressure to furnish the crude product. This material was purified by column chromatography (30% EtOAc/hexanes) to give the title compound 14.2 mg, (32%) as a white solid: 1H NMR (DMSO): δ 8.35 (d, J=12 Hz, 2H), 7.79-7.76 (m, 3H), 7.68 (dt, J=20, 3 Hz, 1H), 7.63 (d, J=21 Hz, 2H), 7.52-7.43 (m, 2H), 6.62 (t, J=12 Hz, 1H), 4.77 (bs, 1H), 4.41 (d, J=64 Hz, 2H), 4.17 (bs, 1H), 3.14 (bs, 2H), 2.48 (qt, J=5 Hz, 1H), 1.86 (t, J=9 Hz, 2H), 1.60 (d, J=24 Hz, 1H); MS (M+1)=439.

Workup

  1. concentrationThe resulting solution was concentrated
  2. dissolutionthe residue was dissolved in CH2Cl2 (5 mL)
  3. washThe organic phase was washed with brine (5 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto furnish the crude product
  8. customThis material was purified by column chromatography (30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-a90f22ee11f645bab735ec4b6c5d2cd0
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08772291B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes