Triethylamine → 6-Methoxy-benzo[d]isothiazole-3-carboxylic acid [4-(4-methyl-piperazin-1-ylmethyl)-3-trifluoromethyl-phenyl]-amide

HRID 556357Notes

Reaction equation

HRID 556357 reaction equation
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[C:7]([C:10]([OH:12])=O)=[N:8][S:9][C:5]=2[CH:4]=1.[CH3:15][N:16]1[CH2:21][CH2:20][N:19]([CH2:22][C:23]2[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][C:24]=2[C:30]([F:33])([F:32])[F:31])[CH2:18][CH2:17]1.CCN(CC)CC.CCCP(=O)=O>CN(C=O)C>[CH3:15][N:16]1[CH2:21][CH2:20][N:19]([CH2:22][C:23]2[CH:29]=[CH:28][C:26]([NH:27][C:10]([C:7]3[C:6]4[CH:13]=[CH:14][C:3]([O:2][CH3:1])=[CH:4][C:5]=4[S:9][N:8]=3)=[O:12])=[CH:25][C:24]=2[C:30]([F:33])([F:31])[F:32])[CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 16167369Propylphosphoric anhydrideHCID 46838908AP-24592HCID 666368056-Methoxybenzo[d]isothiazole-3-carboxylic acid

Product 1

HCID 669928876-Methoxy-benzo[d]isothiazole-3-carboxylic acid [4-(4-methyl-piperazin-1-ylmethyl)-3-trifluoromethyl-phenyl]-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared analogousely to step 6.1 from 2.0 g (9.57 mMol) 6-methoxy-benzo[d]isothiazole-3-carboxylic acid, 3.9 g (14.3 mMol) 4-(4-methyl-piperazin-1-ylmethyl)-3-trifluoromethyl-aniline, 13.3 ml (95.7 mMol) Et3N and 11.17 ml (50% in DMF; 19.1 mMol) propylphosphonic anhydride in 100 ml of dry DMF: m.p.: 156° C.; MS: [M+1]+=465.

Sources & evidence

ORD record
ord-abd1e87f040e41bcbe395dc1d49e6f16
Source dataset
uspto-grants-2011_11
Patent number
US08058276B2

Reaction notes

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