Water → {4'-[4-(4-Dimethylsulfamoyl-piperazin-1-ylmethyl)-phenylcarbamoyl]-6-trifluoromethoxy-biphenyl-3-yl}-carboxylic acid tert-butyl ester

HRID 1678501Notes

Reaction equation

HRID 1678501 reaction equation
C(OC(N[C:9]1[CH:10]=[CH:11][C:12]([O:24][C:25]([F:28])([F:27])[F:26])=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([OH:23])=O)=[CH:17][CH:16]=2)[CH:14]=1)=O)(C)(C)C.[CH3:29][N:30]([CH3:48])[S:31]([N:34]1[CH2:39][CH2:38][N:37]([CH2:40][C:41]2[CH:46]=[CH:45][C:44]([NH2:47])=[CH:43][CH:42]=2)[CH2:36][CH2:35]1)(=[O:33])=[O:32].CCN=C=N[CH2:54][CH2:55][CH2:56]N(C)C.[CH:60]1C=CC2N(O)N=NC=2C=1.CN1CC[O:74][CH2:73]C1.[OH2:77]>CN(C=O)C>[C:55]([O:77][C:73]([C:9]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:23])[NH:47][C:44]3[CH:45]=[CH:46][C:41]([CH2:40][N:37]4[CH2:36][CH2:35][N:34]([S:31](=[O:32])(=[O:33])[N:30]([CH3:48])[CH3:29])[CH2:39][CH2:38]4)=[CH:42][CH:43]=3)=[CH:17][CH:16]=2)[C:12]([O:24][C:25]([F:27])([F:28])[F:26])=[CH:11][CH:10]=1)=[O:74])([CH3:56])([CH3:60])[CH3:54]

Participants

8

Reactant 6

HCID 962WaterHCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 282735524-(4-Amino-benzyl)-piperazine-1-sulfonic acid dimethylamideHCID 598223415'-tert-Butoxycarbonylamino-2'-trifluoromethoxy-biphenyl-4-carboxylic acid

Product 1

HCID 67373671{4'-[4-(4-Dimethylsulfamoyl-piperazin-1-ylmethyl)-phenylcarbamoyl]-6-trifluoromethoxy-biphenyl-3-yl}-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5′-tert-butoxycarbonylamino-2′-trifluoromethoxy-biphenyl-4-carboxylic acid (300 mg), 4-(4-amino-benzyl)-piperazine-1-sulfonic acid dimethylamide (226 mg), EDAC (144 mg) and HOBT (103 mg) in dry DMF (3 ml) containing N-methyl morpholine (0.166 ml) was stirred for 16 h. The mixture was then added to water (12 ml) and the resulting solid collected by filtration and dried and used in the following step without purification (558 mg)

Workup

  1. filtrationthe resulting solid collected by filtration
  2. customdried
  3. customused in the following step without purification (558 mg)

Sources & evidence

ORD record
ord-ea056892380d44d4bf87895aaf8d113c
Source dataset
uspto-grants-2011_08
Patent number
US08008303B2

Reaction notes

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