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

反応式

HRID 82081 の反応式
[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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
25 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-565c04c6b64d4925893feadacda4d812
出典データセット
uspto-grants-2014_09
特許番号
US08846698B2

関連ノート

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