Dimethylformamide → HCID 131723236, compound

HRID 1937822Notes

Reaction equation

HRID 1937822 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]([C:25](=[O:29])[N:26]([CH3:28])[CH3:27])[C:12]([NH:14][C@@H:15]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[C:16]([OH:18])=[O:17])=[O:13])=[CH:6][CH:5]=1)(=[NH:3])[NH2:2].Cl.[NH2:31][CH2:32][C:33]1[CH:40]=[CH:39][C:36]([C:37]#[N:38])=[CH:35][CH:34]=1.CN(C)C=O.C(N1CCOCC1)C>>[C:16]([OH:18])(=[O:17])[CH3:15].[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]([C:25]([N:26]([CH3:27])[CH3:28])=[O:29])[C:12]([NH:14][C@H:15]([C:16](=[O:17])[NH:38][CH2:37][C:36]2[CH:39]=[CH:40][C:33]([C:32]#[N:31])=[CH:34][CH:35]=2)[CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[O:13])=[CH:6][CH:5]=1)(=[NH:3])[NH2:2]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 7525EthylmorpholineHCID 99422504-(Aminomethyl)benzonitrile hydrochlorideHCID 11418216HCID 11418216, compound

Product 1

HCID 131723236HCID 131723236, compoundYield 116.1%

Procedure

To a solution of [3-(4-carbamimidoyl-phenyl)-2-(R,S)-dimethylcarbamoyl-propionylamino]-(S)-cyclohexyl-acetic acid (100 mg, 0.248 mmol, example 1 h) and 4-aminomethyl-benzonitrile hydrochloride (37 mg, 0.22 mmol) in dimethylformamide (10 ml) TOTU (79 mg, 0.24 mmol) and N-ethylmorpholine (50 mg, 0.44 mmol) were added at −15° C. The mixture was stirred for 1 hour and then allowed to warm to room temperature. After evaporation the residue was purified by chromatography on Sephadex LH20 employing n-butanol (17): glacial acetic acid (1): water (2) as eluent. Pure fractions were combined. The solvent was evaporated, the residue was taken up in water and the aqueous solution was lyophilized to yield 83 mg (65%) of the desired product. MS m/z: 517.4 (M+H)+.

Workup

  1. customwere added at −15° C
  2. customAfter evaporation the residue
  3. customwas purified by chromatography on Sephadex
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-a462f97332224302aac164f8b3f02331
Source dataset
uspto-grants-2002_05
Patent number
US06395737B1

Reaction notes

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