Trifluoroacetic acid → HCID 10164813, compound

HRID 1819756Notes

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:37]=[C:36]2[C:31]([CH:32]=[N:33][CH:34]=[N:35]2)=[CH:30][CH:29]=1.[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:37]=[C:36]3[C:31]([CH:32]=[N:33][CH:34]=[N:35]3)=[CH:30][CH:29]=1)[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 67313Mafenide Hydrochloride

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

HCID 27292694-Methylsulfonylbenzylamine hydrochloride

HCID 16663769Quinazolin-7-amine

HCID 22242641Methanol--water (1/1)2×

Product 1

HCID 10164813HCID 10164813, compound

Procedure

A20 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, 7-aminoquinazoline (prepared according to the literature procedure of Naff, et. al. J. Am. Chem. Soc. 1951, 73, 1372-1373.) was substituted for ethyl 2-amino-4-methyl-5-thiazole carboxylate. The product was purified by preparatory reverse phase HPLC to yield A20. Analytical HPLC ret. time=2.17 min, [M+H]+=518.30. HPLC conditions: YMC ODS 5μ, 5 mL/min, 4 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 A20
customYMC ODS 5μ, 5 mL/min, 4 min gradient

Sources & evidence

ORD record: ord-4cad1b155a404b8d901dff8192fbdc5f
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601836B2

Reaction notes

Loading…