Trifluoroacetic acid → 5-(2-fluoro-6-(2H-1,2,3-triazol-2-yl)benzoyl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboximidamide

HRID 244030

Reaction equation

HRID 244030 reaction equation
C(OC([N:8]=[C:9]([NH:32]C(=O)OC(C)(C)C)[N:10]1[CH2:17][CH:16]2[CH:12]([CH2:13][N:14]([C:18](=[O:31])[C:19]3[C:24]([N:25]4[N:29]=[CH:28][CH:27]=[N:26]4)=[CH:23][CH:22]=[CH:21][C:20]=3[F:30])[CH2:15]2)[CH2:11]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>O1C=COC=C1>[F:30][C:20]1[CH:21]=[CH:22][CH:23]=[C:24]([N:25]2[N:29]=[CH:28][CH:27]=[N:26]2)[C:19]=1[C:18]([N:14]1[CH2:15][CH:16]2[CH2:17][N:10]([C:9](=[NH:8])[NH2:32])[CH2:11][CH:12]2[CH2:13]1)=[O:31]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 86669172tert-butyl (((tert-butoxycarbonyl)imino)(5-(2-fluoro-6-(2H-1,2,3-triazol-2-yl)benzoyl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)methyl)carbamate

Product 1

HCID 681632625-(2-fluoro-6-(2H-1,2,3-triazol-2-yl)benzoyl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboximidamide

Reagents, catalysts & solvents 1

HCID 789681,4-DioxinSolvent

Procedure

Crude tert-butyl (((tert-butoxycarbonyl)imino)(5-(2-fluoro-6-(2H-1,2,3-triazol-2-yl)benzoyl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)methyl)carbamate was dissolved in dioxin (8 mL) and TFA (3 mL) was added and the reaction was stirred at room temperature overnight to form crude 5-(2-fluoro-6-(2H-1,2,3-triazol-2-yl)benzoyl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboximidamide (214 mg) as a TFA salt which was used directly in Step C.

Sources & evidence

ORD record
ord-dcb4bf08c30444bea949168ca8895268
Source dataset
uspto-grants-2014_02
Patent number
US08653263B2

Linked notes

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