Trifluoroacetic acid → N-[7a-(5-Amino-2-fluoro-phenyl)-4a,5,6,7-tetrahydro-4H-pyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide

HRID 77580Notes

Reaction equation

HRID 77580 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C:9]1[CH:10]=[CH:11][C:12]([F:40])=[C:13]([C:15]23[CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH:20]2[CH2:19][S:18][C:17]([NH:31][C:32](=[O:39])[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[N:16]3)[CH:14]=1>ClCCl>[NH3:8].[NH2:8][C:9]1[CH:10]=[CH:11][C:12]([F:40])=[C:13]([C:15]23[CH2:23][NH:22][CH2:21][CH:20]2[CH2:19][S:18][C:17]([NH:31][C:32](=[O:39])[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[N:16]3)[CH:14]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86762767Tert-butyl 7a-(5-amino-2-fluoro-phenyl)-2-benzamido-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate

Product 2

HCID 222AmmoniaHCID 86762766N-[7a-(5-Amino-2-fluoro-phenyl)-4a,5,6,7-tetrahydro-4H-pyrrolo[3,4-d][1,3]thiazin-2-yl]benzamideYield 196.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (10 mL) is added to a solution of tert-butyl 7a-(5-amino-2-fluoro-phenyl)-2-benzamido-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate (2.013 g, 4.28 mmol) in dichloromethane (30 mL) and the mixture is stirred at room temperature under nitrogen for 4 hours. The solvent removed in vacuo and the crude product is purified with an SCX column using 3:1 dichloromethane:methanol and then 2:1 dichloromethane:7 N ammonia in methanol to give the title compound (1.555 g, 98%). ES/MS (m/e): 371 (M+H).

Workup

  1. customThe solvent removed in vacuo
  2. customthe crude product is purified with an SCX column

Sources & evidence

ORD record
ord-0627357539d24bd09093b16f487d80df
Source dataset
uspto-grants-2014_09
Patent number
US08841293B1

Reaction notes

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