Trifluoroacetic acid → (6-Amino-3-aza-bicyclo[3.1.0]hex-3-yl)-(7-chloro-thieno[3,2-b]pyridin-2-yl)-methanone

HRID 1063215Notes

Reaction equation

HRID 1063215 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][CH:15]1[CH:20]2[CH:16]1[CH2:17][N:18]([C:21]([C:23]1[S:31][C:30]3[C:25](=[N:26][CH:27]=[CH:28][C:29]=3[Cl:32])[CH:24]=1)=[O:22])[CH2:19]2)(C)(C)C>C(Cl)Cl>[NH2:14][CH:15]1[CH:16]2[CH:20]1[CH2:19][N:18]([C:21]([C:23]1[S:31][C:30]3[C:25](=[N:26][CH:27]=[CH:28][C:29]=3[Cl:32])[CH:24]=1)=[O:22])[CH2:17]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69735881{3-[7-Chloro-thieno[3,2-b]pyridine-2-carbonyl]-3-aza-bicyclo[3.1.0]hex-6-yl}-carbamic acid tert-butyl ester

Product 1

HCID 22278660(6-Amino-3-aza-bicyclo[3.1.0]hex-3-yl)-(7-chloro-thieno[3,2-b]pyridin-2-yl)-methanoneYield 119.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2 mL) was added to a suspension of {3-[7-chloro-thieno[3,2-b]pyridine-2-carbonyl]-3-aza-bicyclo[3.1.0]hex-6-yl}-carbamic acid tert-butyl ester (1.43 g, 3.63 mmol) in CH2Cl2. After 24 h the reaction mixture was concentrated, and the resulting oil was purified on silica gel by flash column chromatography CH2Cl2/MeOH (80/20) to afford the title compound as a white solid (1.27 g, 99%). MS: 294.2/296.2 (MH+); HPLC Rf: 3.085 min.; HPLC purity: 97%.

Workup

  1. concentrationAfter 24 h the reaction mixture was concentrated
  2. customthe resulting oil was purified on silica gel by flash column chromatography CH2Cl2/MeOH (80/20)

Sources & evidence

ORD record
ord-4d622814f3cc4c8e8170fe3784be32f4
Source dataset
uspto-grants-2005_11
Patent number
US06964961B2

Reaction notes

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