Phenyl isocyanate → 7-(3-Phenyl-ureido)-benzo[b]thiophene-2-carboxylic acid (5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-amide

HRID 1986657Notes

Reaction equation

HRID 1986657 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[C:8]([O:24][CH3:25])=[C:9]([NH:11][C:12]([C:14]2[S:18][C:17]3[C:19]([NH2:23])=[CH:20][CH:21]=[CH:22][C:16]=3[CH:15]=2)=[O:13])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[C:31]1([N:37]=[C:38]=[O:39])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(#N)C>[C:1]([C:5]1[CH:6]=[C:7]([NH:26][S:27]([CH3:30])(=[O:28])=[O:29])[C:8]([O:24][CH3:25])=[C:9]([NH:11][C:12]([C:14]2[S:18][C:17]3[C:19]([NH:23][C:38]([NH:37][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[O:39])=[CH:20][CH:21]=[CH:22][C:16]=3[CH:15]=2)=[O:13])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 103435957-Amino-benzo[b]thiophene-2-carboxylic acid (5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-amide

Product 1

HCID 103479507-(3-Phenyl-ureido)-benzo[b]thiophene-2-carboxylic acid (5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-amideYield 50.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To an opaque yellow solution of 7-amino-benzo[b]thiophene-2-carboxylic acid (5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-amide (see Example 1) (30 mg, 0.07 mmol) in acetonitrile was added phenyl isocyanate (10 μL, 0.9 mmol). The reaction was heated to 80° C. for 12 h in a sealed tube, then cooled to room temperature. The product precipitated out directly to provide 20 mg (50%) of the title compound.

Workup

  1. temperaturecooled to room temperature
  2. customThe product precipitated out directly

Sources & evidence

ORD record
ord-4adc67c494084060b472bec9b66183e9
Source dataset
uspto-grants-2009_06
Patent number
US07550461B2

Reaction notes

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