Hydrochloric Acid → N-[2-(6-Chloro-3,3-dimethoxy-hexahydrofuro[3,2-b]pyrrole-4-carbonyl)-3-methylbutyl]-4-[5-fluoro-2-(4-methyl-piperazin-1-yl)-thiazol-4-yl]-benzamide

HRID 1366308Notes

Reaction equation

HRID 1366308 reaction equation
C(O[C:6](=[O:28])[NH:7][CH2:8][CH:9]([C:13]([N:15]1[CH2:19][CH:18]([Cl:20])[CH:17]2[O:21][CH2:22][C:23]([O:26][CH3:27])([O:24][CH3:25])[CH:16]12)=[O:14])[CH:10]([CH3:12])[CH3:11])(C)(C)C.C(Cl)(=O)C.Cl.N1C=CC=C1.Cl.[F:40][C:41]1[S:45][C:44]([N:46]2[CH2:51][CH2:50][N:49]([CH3:52])[CH2:48][CH2:47]2)=[N:43][C:42]=1[C:53]1[CH:61]=[CH:60][C:56](C(O)=O)=[CH:55][CH:54]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CO>[Cl:20][CH:18]1[CH2:19][N:15]([C:13]([CH:9]([CH:10]([CH3:11])[CH3:12])[CH2:8][NH:7][C:6](=[O:28])[C:56]2[CH:60]=[CH:61][C:53]([C:42]3[N:43]=[C:44]([N:46]4[CH2:47][CH2:48][N:49]([CH3:52])[CH2:50][CH2:51]4)[S:45][C:41]=3[F:40])=[CH:54][CH:55]=2)=[O:14])[CH:16]2[C:23]([O:24][CH3:25])([O:26][CH3:27])[CH2:22][O:21][CH:17]12

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 21966771Pyrrole hydrochlorideHCID 575519854-[5-Fluoro-2-(4-methyl-piperazin-1-yl)-thiazol-4-yl]-benzoic acidHCID 86626338[2-(6-Chloro-3,3-dimethoxy-hexahydrofuro[3,2-b]pyrrole-4-carbonyl)-3-methylbutyl]-carbamic acid tertbutyl ester

Product 1

HCID 66929964N-[2-(6-Chloro-3,3-dimethoxy-hexahydrofuro[3,2-b]pyrrole-4-carbonyl)-3-methylbutyl]-4-[5-fluoro-2-(4-methyl-piperazin-1-yl)-thiazol-4-yl]-benzamideYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

[2-(6-Chloro-3,3-dimethoxy-hexahydrofuro[3,2-b]pyrrole-4-carbonyl)-3-methylbutyl]-carbamic acid tertbutyl ester (78 mg, 0.185 mmol) was deprotected under acidic conditions (acetyl chloride in methanol) as described in Example 4, and the crude pyrrole hydrochloride intermediate was then coupled with the HCl salt of 4-[5-fluoro-2-(4-methyl-piperazin-1-yl)-thiazol-4-yl]-benzoic acid using the HATU conditions as described in Example 2, which gave the title compound (98 mg, 85%). MS m/z 624.2 (M+H)+.

Sources & evidence

ORD record
ord-bef411ac4e8243d1a5ecf0b48666659f
Source dataset
uspto-grants-2011_02
Patent number
US07893067B2

Reaction notes

Loading…