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 82081

반응식

HRID 82081 반응식
[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]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 204484Propylphosphonic acidHCID 55267809(5-Fluoropyridin-2-yl)acetic acidHCID 70817490(5-aminopyridin-3-yl)(7-tert-butyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)methanone

생성물 1

HCID 70818020N-{5-[(7-tert-Butyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)carbonyl]pyridin-3-yl}-2-(5-fluoropyridin-2-yl)acetamide수율 65%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
25 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-565c04c6b64d4925893feadacda4d812
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846698B2

연결된 노트

불러오는 중…