N,N'-Bis(tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine → HCID 178454244, compound

HRID 74433Notes

Reaction equation

HRID 74433 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([N:18]1[CH:22]=[CH:21][CH:20]=N1)=[N:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:23]1([CH2:29][O:30][C:31]2[CH:32]=C(CN)C=[CH:35][CH:36]=2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>C(#N)C>[C:14]([O:13][C:11](=[O:12])/[N:10]=[C:9](\[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])/[NH:18][CH2:22][C:21]1[CH:20]=[CH:35][CH:36]=[C:31]([O:30][CH2:29][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[CH:32]=1)([CH3:15])([CH3:16])[CH3:17]

Participants

4

Reactant 2

HCID 4428040N,N'-Bis(tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidineHCID 28368432(3-(Cyclohexylmethoxy)phenyl)methanamine

Product 1

HCID 178454244HCID 178454244, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of N,N′-bis(tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine (0.71 g, 2.28 mmol) and (3-(cyclohexylmethoxy)phenyl)methanamine (0.50 g, 2.28 mmol) in acetonitrile (15 ml) was stirred at 50° C. for 18 h under argon. After cooling to room temperature, a white solid was formed, collected via filtration, and dried under vacuum to give (Z)-tert-butyl(tert-butoxycarbonylamino)(3-(cyclohexylmethoxy)benzylamino)methylenecarbamate. Yield (400 mg, 38%). 1H NMR (400 MHz, DMSO-d6) δ 11.47 (s, 1H), 8.61 (t, J=6.0 Hz, 1H), 7.20 (t, J=8.0 Hz, 1H), 6.77-6.86 (m, 3H), 4.44 (d, J=5.6 Hz, 2H), 3.72 (d, J=6.4 Hz, 2H), 1.60-1.80 (m, 6H), 1.45 (s, 9H), 1.36 (s, 9H), 0.95-1.25 (m, 5H).

Workup

  1. customa white solid was formed
  2. filtrationcollected via filtration
  3. customdried under vacuum

Sources & evidence

ORD record
ord-dc8bca16759e49cab52c42b5d267bbcc
Source dataset
uspto-grants-2014_09
Patent number
US08829244B2

Reaction notes

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