Triethylamine → 3-((4-(4-amino-5-chloro-2-methoxybenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide

HRID 1878350Notes

Reaction equation

HRID 1878350 reaction equation
CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O.[NH2:19][C:20]1[C:28]([Cl:29])=[CH:27][C:23]([C:24]([OH:26])=O)=[C:22]([O:30][CH3:31])[CH:21]=1.[C:32]([NH:36][C:37](=[O:51])[C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([CH2:44][N:45]2[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]2)[CH:39]=1)([CH3:35])([CH3:34])[CH3:33].C(N(CC)CC)C>ClCCl>[NH2:19][C:20]1[C:28]([Cl:29])=[CH:27][C:23]([C:24]([N:48]2[CH2:47][CH2:46][N:45]([CH2:44][C:40]3[CH:39]=[C:38]([CH:43]=[CH:42][CH:41]=3)[C:37]([NH:36][C:32]([CH3:34])([CH3:35])[CH3:33])=[O:51])[CH2:50][CH2:49]2)=[O:26])=[C:22]([O:30][CH3:31])[CH:21]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 816264-Amino-5-chloro-2-methoxybenzoic acidHCID 111923Propylphosphonic anhydrideHCID 66877987N-tert-butyl-3-(piperazin-1-ylmethyl)benzamide

Product 1

HCID 579175773-((4-(4-amino-5-chloro-2-methoxybenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamideYield 74.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Propanephosphonic acid cyclic anhydride (6.31 g, 9.92 mmol, 5.91 ml) was added dropwise to a solution of 4-amino-5-chloro-2-methoxybenzoic acid (1 g, 5 mmol), N-tert-butyl-3-(piperazin-1-ylmethyl)benzamide (1.5150 g, 5,5 mol) and triethylamine (1.508 g, 14.88 mmol, 2.068 mL) in dichloromethane. The reaction was stirred at room temperature for 1 hour. The reaction was concentrated under reduced pressure and the residue was taken up with ethyl acetate, washed with water, sodium hydrogen carbonate and brine. The organic phase was concentrated under vacuum to afford the title compound (1.71 g). MS (ESI) m/z 459.7 [M+H]+

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. washwashed with water, sodium hydrogen carbonate and brine
  3. concentrationThe organic phase was concentrated under vacuum

Sources & evidence

ORD record
ord-fb990f8d4c8b4da091dbd0437db9ff1c
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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