Phenyl isocyanate → HCID 86587513, compound

HRID 2296678Notes

Reaction equation

HRID 2296678 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[S:21][C:20]([S:22]([N:25]3[CH2:30][CH2:29][NH:28][CH2:27][C@@H:26]3[C:31]([NH:33][O:34][CH:35]3[CH2:40][CH2:39][CH2:38][CH2:37][O:36]3)=[O:32])(=[O:24])=[O:23])=[CH:19][CH:18]=2)=[CH:13][CH:12]=1>C(Cl)(Cl)Cl>[F:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[S:21][C:20]([S:22]([N:25]3[CH2:30][CH2:29][N:28]([C:8]([NH:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[O:9])[CH2:27][C@@H:26]3[C:31]([NH:33][O:34][CH:35]3[CH2:40][CH2:39][CH2:38][CH2:37][O:36]3)=[O:32])(=[O:23])=[O:24])=[CH:19][CH:18]=2)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 53817994HCID 53817994, compound

Product 1

HCID 86587513HCID 86587513, compoundYield 108.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of phenyl isocyanate (38 mg) in CHCl3 (1 ml) was added to a solution of (2R)-1-[5-(4-fluorophenyl)thiophene-2-sulfonyl]-N-(2-tetrahydropyranyloxy)-2-piperazinecarboxamide (150 mg) in CHCl3 (3 ml). After stirring for 30 minutes at ambient temperature, the reaction mixture was concentrated in vacuo to give 203 mg of (2R)-1-[5-(4-fluorophenyl)thiophene-2-sulfonyl ]-4-[(N-phenyl) aminocarbonyl]-N-(2-tetrahydropyranyloxy)-2-piperazinecarboxamide as an amorphous powder.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-f8120e104fc94a75be2cd8a7d472f360
Source dataset
uspto-grants-2002_12
Patent number
US06489324B2

Reaction notes

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