(r)-Tert-butyl 2-(5-(4-carbamoyl-1h-benzimidazol-2-yl)thiophen-2-yl)pyrrolidine-1-carboxylate → 2-(5-((2r)-Pyrrolidin-2-yl)thien-2-yl)-1h-benzimidazole-4-carboxamide

HRID 564222Notes

Reaction equation

HRID 564222 reaction equation
[C:1]([C:4]1[C:12]2[N:11]=[C:10]([C:13]3[S:17][C:16]([C@H:18]4[CH2:22][CH2:21][CH2:20][N:19]4C(OC(C)(C)C)=O)=[CH:15][CH:14]=3)[NH:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:3])[NH2:2]>C(O)(C(F)(F)F)=O>[NH:19]1[CH2:20][CH2:21][CH2:22][C@@H:18]1[C:16]1[S:17][C:13]([C:10]2[NH:9][C:8]3[CH:7]=[CH:6][CH:5]=[C:4]([C:1]([NH2:2])=[O:3])[C:12]=3[N:11]=2)=[CH:14][CH:15]=1

Participants

3

Reactant 1

HCID 66760174(r)-Tert-butyl 2-(5-(4-carbamoyl-1h-benzimidazol-2-yl)thiophen-2-yl)pyrrolidine-1-carboxylate

Product 1

HCID 667602372-(5-((2r)-Pyrrolidin-2-yl)thien-2-yl)-1h-benzimidazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of EXAMPLE 16C (2.2 g) in TFA (50 mL) was stirred at ambient temperature for 30 minutes. After concentration, the concentrate was purified by HPLC (Zorbax, C-18, Mobile phase A: 0.1% TFA in water; B: 0.1% TFA in acetonitrile; 0-100% gradient). 1H NMR (CD3OD) δ 2.19-2.29 (m, 1H), 2.28-2.41 (m, 2H), 2.55-2.67 (m, 1H), 3.43-3.56 (m, 2H), 5.01 (dd, J=9.3, 6.9 Hz, 1H), 7.36 (d, J=3.7 Hz, 1H), 7.39 (d, J=4.6 Hz, 1H), 7.71 (d, J=7.6 Hz, 1H), 7.79 (d, J=3.7 Hz, 1H), 7.93 (d, J=7.6 Hz, 1H).

Workup

  1. concentrationAfter concentration
  2. customthe concentrate was purified by HPLC (Zorbax, C-18, Mobile phase A: 0.1% TFA in water; B: 0.1% TFA in acetonitrile; 0-100% gradient)

Sources & evidence

ORD record
ord-edad611345c747de890628520adfdc5c
Source dataset
uspto-grants-2011_11
Patent number
US08067613B2

Reaction notes

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