4-Chlorobenzylamine → [2-(4-Chloro-benzylamino)-thiazol-5-yl]-(1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone

HRID 2261606Notes

Reaction equation

HRID 2261606 reaction equation
Br[C:2]1[S:3][C:4]([C:7]([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=3)[NH:11][CH:10]=2)=[O:8])=[CH:5][N:6]=1.[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH2:24])=[CH:21][CH:20]=1.C(N(CC)C(C)C)(C)C>O>[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH:24][C:2]2[S:3][C:4]([C:7]([C:9]3[C:17]4[C:12](=[N:13][CH:14]=[CH:15][CH:16]=4)[NH:11][CH:10]=3)=[O:8])=[CH:5][N:6]=2)=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 660364-ChlorobenzylamineHCID 81531DiisopropylethylamineHCID 59593307(2-Bromo-1,3-thiazol-5-yl)(1H-pyrrolo[2,3-b]pyridin-3-yl)methanone

Product 1

HCID 59593357[2-(4-Chloro-benzylamino)-thiazol-5-yl]-(1H-pyrrolo[2,3-b]pyridin-3-yl)-methanoneYield 30%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of (2-Bromo-thiazol-5-yl)-(1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone (99, 5 mg, 0.02 mmol), p-chlorobenzylamine (61, 10 mg, 0.08 mmol), and N,N-Diisopropylethylamine (10 μL, 0.08 mmol) in tetrahydrfuran (10 mL), in a sealed reaction vessel, was stirred room temperature overnight. The reaction mixture was poured into iced water, extracted with ethyl acetate, washed with brine, and dried over magnesium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography eluting with ethyl acetate in hexane to provide the compound as a light yellow solid (P-0077, 2 mg, 30%). MS (ESI) [M+H+]=305.90, 307.88.

Workup

  1. customin a sealed reaction vessel
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. customAfter removal of solvent
  6. customthe residue was purified by silica gel column chromatography
  7. washeluting with ethyl acetate in hexane

Sources & evidence

ORD record
ord-322ffffd4e4d47e4829819fe60f45a53
Source dataset
uspto-grants-2010_12
Patent number
US07846941B2

Reaction notes

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