N,N'-Di-Boc-1H-pyrazole-1-carboximidamide → HCID 178485742, compound

HRID 1441376Notes

Reaction equation

HRID 1441376 reaction equation
[CH3:1][NH:2][C:3]([C@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=1)=[O:4].[C:17]([O:21][C:22](=[O:38])[NH:23]/[C:24](/N1C=CC=N1)=[N:25]/[C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:20])([CH3:19])[CH3:18]>C(Cl)Cl>[C:28]([O:27][C:26]([NH:25]/[C:24](/[NH:16][C:13]1[CH:12]=[CH:11][C:10]([N:6]2[CH2:7][CH2:8][CH2:9][C@@H:5]2[C:3]([NH:2][CH3:1])=[O:4])=[CH:15][CH:14]=1)=[N:23]/[C:22]([O:21][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:38])=[O:32])([CH3:31])([CH3:30])[CH3:29]

Participants

4

Reactant 2

HCID 6383521N,N'-Di-Boc-1H-pyrazole-1-carboximidamideHCID 68685541(R)-1-(4-Amino-phenyl)-pyrrolidine-2-carboxylic acid methylamide

Product 1

HCID 178485742HCID 178485742, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (R)-1-(4-amino-phenyl)-pyrrolidine-2-carboxylic acid methylamide (Method 57; 1.0 g, 4.5 mmol) in DCM (60 ml) was added di-tert-butyl[(Z)-1H-pyrazol-1-ylmethylylidene]biscarbamate (1.7 g, 5.5 mmol) in one portion. The reaction was stirred overnight before removal of the solvent in vacuo. The residue was purified via column chromatography eluting with 20% EtOAc/isohexane, 50% EtOAc/iso-hexne and finally 100% EtOAc. The title compound was obtained as a white foam (1.9 g, 91%).

Workup

  1. customThe residue was purified via column chromatography
  2. washeluting with 20% EtOAc/isohexane, 50% EtOAc/iso-hexne and finally 100% EtOAc

Sources & evidence

ORD record
ord-7c11ee66c6e04c1ab87673cb73437903
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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