N,N'-Di-Boc-1H-pyrazole-1-carboximidamide → HCID 178454299, compound

HRID 1441380Notes

Reaction equation

HRID 1441380 reaction equation
[CH:1]1([NH:4][C:5]([C@H:7]2[CH2:11][CH2:10][CH2:9][N:8]2[C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=2)=[O:6])[CH2:3][CH2:2]1.[C:19]([O:23][C:24](=[O:40])[NH:25]/[C:26](/N1C=CC=N1)=[N:27]/[C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:22])([CH3:21])[CH3:20]>C(Cl)Cl>[C:30]([O:29][C:28]([NH:27]/[C:26](/[NH:18][C:15]1[CH:14]=[CH:13][C:12]([N:8]2[CH2:9][CH2:10][CH2:11][C@@H:7]2[C:5]([NH:4][CH:1]2[CH2:2][CH2:3]2)=[O:6])=[CH:17][CH:16]=1)=[N:25]/[C:24]([O:23][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:40])=[O:34])([CH3:33])([CH3:32])[CH3:31]

Participants

4

Reactant 2

HCID 6383521N,N'-Di-Boc-1H-pyrazole-1-carboximidamideHCID 68689756(R)-1-(4-Amino-phenyl)-pyrrolidine-2-carboxylic acid cyclopropylamide

Product 1

HCID 178454299HCID 178454299, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-1-(4-Amino-phenyl)-pyrrolidine-2-carboxylic acid cyclopropylamide (Method 61; 1.2 g, 4.9 mmol) in DCM (60 ml) was added di-tert-butyl[(Z)-1H-pyrazol-1-ylmethylylidene]biscarbamate (1.9 g, 6.1 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% ethylactetate/isohexane, 50% EtOAc/isohexane and finally 100% EtOAc. The title compound was obtained as a white foam (2.0 g, 81%). NMR (299.954 MHz, CDCl3) 11.63 (s, 1H), 10.09 (s, 1H), 7.60 (s, 1H), 7.40 (d, 2H), 6.45 (m, 3H), 3.92 (t, 1H), 3.59 (t, 1H), 3.19 (q, 1H), 2.69 (m, 1H), 2.29-2.22 (m, 2H), 2.03-1.84 (m, 2H), 1.53 (s, 9H), 1.49 (s, 9H), 0.80-0.68 (m, 2H), 0.44-0.32 (m, 2H); m/z 488.

Workup

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

Sources & evidence

ORD record
ord-79686abf1e7840c9a0d4129d9d6b1ead
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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