Triethylamine → HCID 123783014, compound

HRID 921099Notes

Reaction equation

HRID 921099 reaction equation
[CH2:1]([O:4][C:5]1([CH3:41])[CH2:10][CH2:9][N:8]([C:11]2[N:16]3[N:17]=[C:18]([CH2:20][O:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4Br)[CH:19]=[C:15]3[N:14]=[C:13]([CH3:30])[C:12]=2[C@H:31]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])[C:32]([O:34][CH3:35])=[O:33])[CH2:7][CH2:6]1)[CH:2]=[CH2:3].CCN(CC)CC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:37]([O:36][C@@H:31]([C:12]1[C:13]([CH3:30])=[N:14][C:15]2=[CH:19][C:18]3=[N:17][N:16]2[C:11]=1[N:8]1[CH2:9][CH2:10][C:5]([CH3:41])([O:4][CH2:1][CH:2]=[CH:3][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[CH2:22][O:21][CH2:20]3)[CH2:6][CH2:7]1)[C:32]([O:34][CH3:35])=[O:33])([CH3:40])([CH3:39])[CH3:38]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 118307140HCID 118307140, compound

Product 1

HCID 123783014HCID 123783014, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of (S)-methyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(((2-bromobenzyl)oxy)methyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (0.025 g, 0.040 mmol) in acetonitrile (1 ml) in a pressure tube were added Et3N (0.055 ml, 0.397 mmol), triphenylphosphine (3.12 mg, 0.012 mmol) and tris(dibenzylideneacetone)dipalladium (0) (3.64 mg, 3.97 μmol). The tube was sealed and the mixture was stirred at 120° C. After 18 h, the dark mixture was cooled and concentrated. The brown residue was purified by flash chromatography (Biotage; 0%-60% EtOAc/hexane; 20 CV) to afford the title compound as mixture of cis- and trans-isomers (16.9 mg, 0.031 mmol, 78% yield) as a pale yellow oil. LCMS (M+H) calcd for C31H41N4O5: 549.30. found: 549.4.

Workup

  1. customThe tube was sealed
  2. temperaturethe dark mixture was cooled
  3. concentrationconcentrated
  4. customThe brown residue was purified by flash chromatography (Biotage; 0%-60% EtOAc/hexane; 20 CV)

Sources & evidence

ORD record
ord-7ea82a26c0f84539a04691ebb05408c8
Source dataset
uspto-grants-2016_03
Patent number
US09273067B2

Reaction notes

Loading…