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 1258496Notes

Reaction equation

HRID 1258496 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-7ca427071afb43c19243094cd5f110cf
Source dataset
uspto-grants-2013_06
Patent number
US08466158B2

Reaction notes

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