Dimethylformamide → HCID 70003779, compound

HRID 1266705Notes

Reaction equation

HRID 1266705 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:31])[CH:6]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([C:28](=[NH:30])[NH2:29])=[CH:24][CH:23]=1)[C:7]1[CH:12]=[C:11]([O:13][CH2:14][CH3:15])[C:10]([O:16][CH2:17][CH2:18][OH:19])=[CH:9][C:8]=1[F:20])[CH3:3].CN(C=O)C.C(N(CC)CC)C.[C:44]1([N:50]=[C:51]=[O:52])[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>C1COCC1>[CH2:2]([O:4][C:5](=[O:31])[CH:6]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([NH2:29])=[N:30][C:51](=[O:52])[NH:50][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[CH:24][CH:23]=1)[C:7]1[CH:12]=[C:11]([O:13][CH2:14][CH3:15])[C:10]([O:16][CH2:17][CH2:18][OH:19])=[CH:9][C:8]=1[F:20])[CH3:3]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 70002371HCID 70002371, compound

Product 1

HCID 70003779HCID 70003779, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The (RS)-(4-carbamimidoyl-phenylamino)-[5-ethoxy-2-fluoro-4-(2-hydroxy-ethoxy)-phenyl]-acetic acid ethyl ester hydrochloride (456 mg) described in example 1.6 was dissolved in THF (3 ml). DMF (3 ml), triethylamine (106 mg) and phenylisocyanate (131 mg) were added and the mixture was stirred for 3 h at room temperature. The reaction mixture was concentrated and purified by column chromatography (hexane/ethyl acetate) to give 380 mg of (RS)-[4-(Amino-phenylcarbamoylimino-methyl)-phenylamino]-[5-ethoxy-2-fluoro-4-(2-hydroxy-ethoxy)-phenyl]-acetic acid ethyl ester as a colorless foam. MS: 539 ([M+H]+).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-a39ae50b1f3e4bf5b8d8806800e41b32
Source dataset
uspto-grants-2003_04
Patent number
US06548694B2

Reaction notes

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