Triethylamine → N-{5-[(7-tert-Butyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)carbonyl]pyridin-3-yl}-2-(5-fluoropyridin-2-yl)acetamide

HRID 82081Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([OH:11])=O)=[N:6][CH:7]=1.[NH2:12][C:13]1[CH:14]=[C:15]([C:19]([C:21]2[C:29]3[CH:28]=[N:27][CH:26]=[N:25][C:24]=3[N:23]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH:22]=2)=[O:20])[CH:16]=[N:17][CH:18]=1.CCCP(O)(O)=O.C(N(CC)CC)C>C1COCC1>[C:30]([N:23]1[C:24]2[N:25]=[CH:26][N:27]=[CH:28][C:29]=2[C:21]([C:19]([C:15]2[CH:14]=[C:13]([NH:12][C:9](=[O:11])[CH2:8][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][N:6]=3)[CH:18]=[N:17][CH:16]=2)=[O:20])=[CH:22]1)([CH3:33])([CH3:31])[CH3:32]

Participants

Conditions

Temperature: 25 °C

Procedure

2-(5-Fluoropyridin-2-yl)acetic acid (23.1 mg, 0.149 mmol) (see Preparation 92) was added to (5-aminopyridin-3-yl)(7-tert-butyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)methanone (40 mg, 0.135 mmol) (see Preparation 31), 1-propylphosphonic acid cyclic anhydride (0.2 mL, 0.338 mmol, 50% in EtOAc) and triethylamine (0.65 mL, 0.474 mmol) in THF (3 mL). The mixture was stirred at 25° C. for 18 hours, evaporated in vacuo and partitioned between saturated aqueous sodium bicarbonate (5 mL) and ethyl acetate (5 mL). The organic phase was dried over sodium sulfate, evaporated in vacuo and the residue was triturated with pentane:diethyl ether (3:1, 1 mL) to afford the title compound as an off white solid in 65% yield, 38 mg.

Workup

customevaporated in vacuo
custompartitioned between saturated aqueous sodium bicarbonate (5 mL) and ethyl acetate (5 mL)
dry with materialThe organic phase was dried over sodium sulfate
customevaporated in vacuo
customthe residue was triturated with pentane:diethyl ether (3:1, 1 mL)

Sources & evidence

ORD record: ord-565c04c6b64d4925893feadacda4d812
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846698B2

Reaction notes

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