Trifluoroacetic acid → HCID 10207991, compound

HRID 1794653Notes

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[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[N:34]=[CH:33][CH:32]=[CH:31]2.[NH2:38][C:39]1S[C:41]([C:45]([O:47][CH2:48]C)=O)=[C:42]([CH3:44])[N:43]=1.[C:50](O)(C(F)(F)F)=[O:51].O.[CH3:58]O>>[CH3:50][O:51][C:26]1[CH:19]=[C:44]2[C:42](=[CH:41][C:45]=1[O:47][CH3:48])[N:43]=[C:39]([NH:27][C:28]1[CH:29]=[C:30]3[C:35](=[CH:36][CH:37]=1)[N:34]=[CH:33][CH:32]=[CH:31]3)[N:38]=[C:58]2[NH:11][CH2:10][C:9]1[CH:8]=[CH:7][C:6]([S:3]([NH2:2])(=[O:4])=[O:5])=[CH:13][CH:12]=1

Participants

Reactant 6

HCID 6422Trifluoroacetic acid2×

HCID 113736-Aminoquinoline

HCID 67313Mafenide Hydrochloride

HCID 343747Ethyl 2-amino-4-methylthiazole-5-carboxylate

HCID 27292694-Methylsulfonylbenzylamine hydrochloride

HCID 22242641Methanol--water (1/1)2×

Product 1

HCID 10207991HCID 10207991, compound

Procedure

A19 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, 6-aminoquinoline was substituted for ethyl 2-amino-4-methyl-5-thiazole carboxylate. The product was purified by preparatory reverse phase HPLC to yield A19. Analytical HPLC ret. time=1.09 min, [M+H]+=517.12. HPLC conditions: phenomenex primesphere 5 u C18 4.6×30 mm column, 5 mL/min, 2 min gradient, at 254 nm 0–100% B in A(A; 0.1% TFA in 90/10 water/methanol; B; 0.1% TFA in 10/90 water/methanol)

Workup

customThe product was purified by preparatory reverse phase HPLC
customto yield A19
customC18 4.6×30 mm column, 5 mL/min, 2 min gradient

Sources & evidence

ORD record: ord-200c4ba7c4624c48801e6832dd700c9a
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07022849B2

Reaction notes

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