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4-Cyclopropylbenzoyl chloride → 4-{4-[3-(4-Cyclopropyl-benzoylamino)-4-fluoro-phenyl]-7H-pyrrolo[2,3-d]pyrimidin-6-yl}-3,6-dihydro-2H-pyridine-1-carboxylic acid dimethylamide

HRID 589493
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HRID 589493 반응식
[CH3:1][N:2]([CH3:28])[C:3]([N:5]1[CH2:10][CH:9]=[C:8]([C:11]2[NH:27][C:14]3[N:15]=[CH:16][N:17]=[C:18]([C:19]4[CH:24]=[CH:23][C:22]([F:25])=[C:21]([NH2:26])[CH:20]=4)[C:13]=3[CH:12]=2)[CH2:7][CH2:6]1)=[O:4].[CH:29]1([C:32]2[CH:40]=[CH:39][C:35]([C:36](Cl)=[O:37])=[CH:34][CH:33]=2)[CH2:31][CH2:30]1>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[CH3:1][N:2]([CH3:28])[C:3]([N:5]1[CH2:6][CH:7]=[C:8]([C:11]2[NH:27][C:14]3[N:15]=[CH:16][N:17]=[C:18]([C:19]4[CH:24]=[CH:23][C:22]([F:25])=[C:21]([NH:26][C:36](=[O:37])[C:35]5[CH:39]=[CH:40][C:32]([CH:29]6[CH2:31][CH2:30]6)=[CH:33][CH:34]=5)[CH:20]=4)[C:13]=3[CH:12]=2)[CH2:9][CH2:10]1)=[O:4]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 441909384-Cyclopropylbenzoyl chlorideHCID 867309864-[4-(3-Amino-4-fluoro-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid dimethylamide

생성물 1

HCID 712307634-{4-[3-(4-Cyclopropyl-benzoylamino)-4-fluoro-phenyl]-7H-pyrrolo[2,3-d]pyrimidin-6-yl}-3,6-dihydro-2H-pyridine-1-carboxylic acid dimethylamide

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매
HCID 1049
Pyridine
용매

실험 절차

A mixture of Intermediate 10 (80 mg, 0.210 mmol), 4-cyclopropyl-benzoyl chloride (J. Med. Chem., 52(14), 4329-4337; 2009) (76 mg, 0.421 mmol), and DMAP (2.6 mg, 0.021 mmol) in pyridine (2 ml) was stirred at r.t. overnight. The mixture was evaporated to dryness, then sat. aqueous NaHCO3 was added, and the mixture was extracted with DCM. The organic layer was dried, filtered, and evaporated to dryness. The residue was purified by flash chromatography (silica gel, EtOAc/MeOH/NH3 gradient) to obtain Example 20.

후처리

  1. customThe mixture was evaporated to dryness
  2. additionsat. aqueous NaHCO3 was added
  3. extractionthe mixture was extracted with DCM
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was purified by flash chromatography (silica gel, EtOAc/MeOH/NH3 gradient)
  8. customto obtain Example 20

출처 및 근거

ORD 기록
ord-b2fe64dfa8b74ed9b5ba63e21ce70571
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09233111B2

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