Trifluoroacetic acid → HCID 10145617, compound

HRID 1794650Notes

Reaction equation

HRID 1794650 reaction equation
Cl.[NH2:2][S:3]([C:6]1[CH:13]=[CH:12][C:9]([CH2:10][NH2:11])=[CH:8][CH:7]=1)(=[O:5])=[O:4].Cl.CS([C:19]1[CH:26]=CC(CN)=CC=1)(=O)=O.[NH2:27][C:28]1[S:29][C:30]([C:37]([O:39][CH2:40][CH3:41])=[O:38])=[C:31]([C:33]([F:36])([F:35])[F:34])[N:32]=1.[NH2:42][C:43]1S[C:45]([C:49]([O:51][CH2:52]C)=O)=[C:46]([CH3:48])[N:47]=1.[C:54](O)(C(F)(F)F)=[O:55].O.[CH3:62]O>>[NH2:2][S:3]([C:6]1[CH:7]=[CH:8][C:9]([CH2:10][NH:11][C:62]2[C:48]3[C:46](=[CH:45][C:49]([O:51][CH3:52])=[C:26]([O:55][CH3:54])[CH:19]=3)[N:47]=[C:43]([NH:27][C:28]3[S:29][C:30]([C:37]([O:39][CH2:40][CH3:41])=[O:38])=[C:31]([C:33]([F:36])([F:34])[F:35])[N:32]=3)[N:42]=2)=[CH:12][CH:13]=1)(=[O:4])=[O:5]

Participants

7

Reactant 6

HCID 6422Trifluoroacetic acid2×HCID 67313Mafenide HydrochlorideHCID 676565-Thiazolecarboxylic acid, 2-amino-4-(trifluoromethyl)-, ethyl esterHCID 343747Ethyl 2-amino-4-methylthiazole-5-carboxylateHCID 27292694-Methylsulfonylbenzylamine hydrochlorideHCID 22242641Methanol--water (1/1)2×

Product 1

HCID 10145617HCID 10145617, compound

Procedure

A14 was prepared in an manner analogous to example A1 with the exception that in step A1.1 4-aminosulfonylbenzylamine hydrochloride was substituted for 4-methylsulfonylbenzylamine hydrochloride, and in step A1.2 ethyl 2-amino-4-trifluoromethyl-5-thiazole carboxylate was substituted for ethyl 2-amino-4-methyl-5-thiazole carboxylate. LCMS=Ret. Time=1.61 min*, M+=613.20* HPLC conditions used to determine retention times; 2 min gradient 0–100% B in A(A; 0.1% TFA in 90/10 water/methanol; B; 0.1% TFA in 10/90 water/methanol) using a TMC turbopack column at 220 nm.

Workup

  1. custom2 min gradient 0–100% B

Sources & evidence

ORD record
ord-62820a03831c46abab32b610abb37ced
Source dataset
uspto-grants-2006_04
Patent number
US07022849B2

Reaction notes

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