Tert-butyl 2-(5-(4-carbamoyl-1h-benzimidazol-2-yl)thiophen-2-yl)pyrrolidine-1-carboxylate → HCID 66760371, compound

HRID 564232Notes

Reaction equation

HRID 564232 reaction equation
[C:1]([C:4]1[C:12]2[N:11]=[C:10]([C:13]3[S:17][C:16]([CH: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]>ClCCl.C(O)(C(F)(F)F)=O>[NH:19]1[CH2:20][CH2:21][CH2:22][CH: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

4

Reactant 1

HCID 66759375Tert-butyl 2-(5-(4-carbamoyl-1h-benzimidazol-2-yl)thiophen-2-yl)pyrrolidine-1-carboxylate

Product 1

HCID 66760371HCID 66760371, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of EXAMPLE 34D (2.1 g) in dichloromethane (20 mL) and TFA (5 mL) was stirred at ambient temperature overnight and concentrated. 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 2.19-2.27 (m, 1H), 2.27-2.41 (m, 2H), 2.57-2.68 (m, 1H), 3.43-3.57 (m, 2H), 5.01 (dd, J=9.4, 6.9 Hz, 1H), 7.36 (t, J=7.7 Hz, 1H), 7.42 (d, J=4.6 Hz, 1H), 7.73 (dd, J=8.1, 1.1 Hz, 1H), 7.81 (d, J=4.0 Hz, 1H), 7.94 (dd, J=7.7, 0.9 Hz, 1H).

Workup

  1. concentrationconcentrated
  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-af9cc4f97d824d3691c2183f22c4d562
Source dataset
uspto-grants-2011_11
Patent number
US08067613B2

Reaction notes

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