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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
Notes
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Reaction equation

HRID 589493 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 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

Product 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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridine
Catalyst
HCID 1049PyridineSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b2fe64dfa8b74ed9b5ba63e21ce70571
Source dataset
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09233111B2

Reaction notes

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