Triethylamine → Pyrimidine-5-carboxylic acid-{1-[3-fluoro-4-(4-methoxy-phenoxy)-benzylcarbamoyl]-cyclopropyl}-amide

HRID 1406337Notes

Reaction equation

HRID 1406337 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)[CH2:5][NH2:6].[N:19]1[CH:24]=[C:23]([C:25]([NH:27][C:28]2([C:31](O)=[O:32])[CH2:30][CH2:29]2)=[O:26])[CH:22]=[N:21][CH:20]=1.C(N(CC)CC)C>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)[CH2:5][NH:6][C:31]([C:28]1([NH:27][C:25]([C:23]2[CH:22]=[N:21][CH:20]=[N:19][CH:24]=2)=[O:26])[CH2:30][CH2:29]1)=[O:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 289662543-Fluoro-4-(4-methoxy-phenoxy)-benzylamineHCID 594962911-[(Pyrimidine-5-carbonyl)-amino]cyclopropanecarboxylic acid

Product 1

HCID 25232245Pyrimidine-5-carboxylic acid-{1-[3-fluoro-4-(4-methoxy-phenoxy)-benzylcarbamoyl]-cyclopropyl}-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

24.7 mg (0.1 mmol) of 3-fluoro-4-(4-methoxy-phenoxy)-benzylamine were dissolved in 1 ml DMF. 20.7 mg (0.1 mmol) of 1-[(pyrimidine-5-carbonyl)-amino]-cyclopropanecarboxylic acid (prepared in 1b) were also dissolved in DMF and 35.3 mg (0.11 mmol) and 21 μl triethylamine (0.15 mmol) were added. Shaken overnight at ambient temperature and purified by reversed-phase chromatography.

Workup

  1. custompurified by reversed-phase chromatography

Sources & evidence

ORD record
ord-343dc22a021f4ef683152d393226b087
Source dataset
uspto-grants-2014_12
Patent number
US08916589B2

Reaction notes

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