1,1'-Carbonyldiimidazole → Tert-butyl 2-(5-(4-carbamoyl-1h-benzimidazol-2-yl)thiophen-2-yl)pyrrolidine-1-carboxylate

HRID 564231Notes

Reaction equation

HRID 564231 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]1[S:17][C:16]([C:18](O)=O)=[CH:15][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1N=CN(C(N2C=NC=C2)=O)C=1.Cl.Cl.[NH2:35][C:36]1[C:44]([NH2:45])=[CH:43][CH:42]=[CH:41][C:37]=1[C:38]([NH2:40])=[O:39]>N1C=CC=CC=1.CN(C=O)C>[C:38]([C:37]1[C:36]2[N:35]=[C:18]([C:16]3[S:17][C:13]([CH:9]4[CH2:10][CH2:11][CH2:12][N:8]4[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[CH:14][CH:15]=3)[NH:45][C:44]=2[CH:43]=[CH:42][CH:41]=1)(=[O:39])[NH2:40]

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 534228072,3-Diaminobenzamide dihydrochlorideHCID 667594261103394-61-1

Product 1

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

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of EXAMPLE 34C (2.4 g) in pyridine (100 mL) and DMF (100 mL) was added CDI (1.6 g). The mixture was heated at 40° C. for 1 hour, treated with 2,3-diaminobenzamide dihydrochloride (1.8 g), stirred at ambient temperature overnight and concentrated. The concentrate was heated in acetic acid (50 mL) at 80° C. overnight and concentrated. The concentrate was flash chromatographed on silica gel with ethyl acetate.

Workup

  1. concentrationconcentrated
  2. temperatureThe concentrate was heated in acetic acid (50 mL) at 80° C. overnight
  3. concentrationconcentrated
  4. customchromatographed on silica gel with ethyl acetate

Sources & evidence

ORD record
ord-e4c3516133c04d6eb869f061ca26ce0c
Source dataset
uspto-grants-2011_11
Patent number
US08067613B2

Reaction notes

Loading…