Benzocaine → HCID 10187062, compound

HRID 1794652Notes

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:38]=[CH:37][C:31]([C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:30][CH:29]=1.[NH2:39][C:40]1S[C:42]([C:46]([O:48][CH2:49]C)=O)=[C:43]([CH3:45])[N:44]=1.[C:51](O)(C(F)(F)F)=[O:52].O.[CH3:59]O>>[NH2:2][S:3]([C:6]1[CH:7]=[CH:8][C:9]([CH2:10][NH:11][C:59]2[C:45]3[C:43](=[CH:42][C:46]([O:48][CH3:49])=[C:26]([O:52][CH3:51])[CH:19]=3)[N:44]=[C:40]([NH:27][C:28]3[CH:29]=[CH:30][C:31]([C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:37][CH:38]=3)[N:39]=2)=[CH:12][CH:13]=1)(=[O:4])=[O:5]

Participants

Reactant 6

HCID 2337Benzocaine

HCID 6422Trifluoroacetic acid2×

HCID 67313Mafenide Hydrochloride

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

HCID 27292694-Methylsulfonylbenzylamine hydrochloride

HCID 22242641Methanol--water (1/1)2×

Product 1

HCID 10187062HCID 10187062, compoundYield 21%

Procedure

A18 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 4-aminobenzoate was substituted for ethyl 2-amino-4-methyl-5-thiazole carboxylate. The product was purified by preparatory reverse phase HPLC to yield A18 in 21% yield. LCMS=Ret. Time=2.87 min*, M+=538.40. * HPLC conditions used to determine retention times; 4 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 YMC ODS S5 column at 220 nm.

Workup

customThe product was purified by preparatory reverse phase HPLC
customto yield A18 in 21% yield
custom4 min gradient 0–100% B

Sources & evidence

ORD record: ord-422f0ab3f5f44c06acbd89c3d4efc7fc
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07022849B2

Reaction notes

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