Triethylamine → HCID 57917582, compound

HRID 1878384Notes

Reaction equation

HRID 1878384 reaction equation
CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O.[C:19]([NH:23][C:24](=[O:39])[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31][N:32]2[CH2:37][CH2:36][NH:35][CH2:34][C@H:33]2[CH3:38])[CH:26]=1)([CH3:22])([CH3:21])[CH3:20].[NH2:40][C:41]1[CH:49]=[CH:48][C:44]([C:45](O)=[O:46])=[CH:43][C:42]=1[F:50].C(N(CC)CC)C>ClCCl>[NH2:40][C:41]1[CH:49]=[CH:48][C:44]([C:45]([N:35]2[CH2:36][CH2:37][N:32]([CH2:31][C:27]3[CH:26]=[C:25]([CH:30]=[CH:29][CH:28]=3)[C:24]([NH:23][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:39])[C@H:33]([CH3:38])[CH2:34]2)=[O:46])=[CH:43][C:42]=1[F:50]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 99714-Amino-3-fluorobenzoic acidHCID 111923Propylphosphonic anhydrideHCID 57917674HCID 57917674, compound

Product 1

HCID 57917582HCID 57917582, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Propanephosphonic acid cyclic anhydride (1.967 g, 3 mmol, 1.840 mL, 50% solution in ethyl acetate) was added dropwise to a solution of (R)N-tert-butyl-3-((2-methylpiperazin-1-yl)methyl)benzamide (500 mg, 1.7 mmol), 4-amino-3-fluorobenzoic acid (239.7 mg, 1.5 mmol) and triethylamine (469 mg, 4.5 mmol, 1.84 mL) in dichloromethane. The reaction was stirred at room temperature for 2 hours. The dichloromethane was removed under reduced pressure and the residue was taken up in ethyl acetate, washed with water, sodium hydrogen carbonate and brine. The organic layer was concentrated under vacuum to afford the title compound (476.3 mg).

Workup

  1. customThe dichloromethane was removed under reduced pressure
  2. washwashed with water, sodium hydrogen carbonate and brine
  3. concentrationThe organic layer was concentrated under vacuum

Sources & evidence

ORD record
ord-c47a4f4b93fe4c72b12dd032d618dd2f
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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