N,N'-Bis(tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine → HCID 178454306, compound

HRID 527080Notes

Reaction equation

HRID 527080 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][CH2:12][C@@H:11]([NH2:15])[CH2:10]2)[C:5]([F:16])=[CH:4][N:3]=1.[C:17]([O:21][C:22]([N:24]=[C:25]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])N1C=CC=N1)=[O:23])([CH3:20])([CH3:19])[CH3:18]>C(Cl)Cl>[C:34]([O:33][C:32]([NH:31][C:25](=[N:24][C:22](=[O:23])[O:21][C:17]([CH3:20])([CH3:19])[CH3:18])[NH:15][C@@H:11]1[CH2:12][CH2:13][CH2:14][C@H:9]([NH:8][C:6]2[C:5]([F:16])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=2)[CH2:10]1)=[O:38])([CH3:37])([CH3:36])[CH3:35]

Participants

4

Reactant 2

HCID 4428040N,N'-Bis(tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidineHCID 86667454(1S,3R)-N1-(2-chloro-5-fluoro-pyrimidin-4-yl)cyclohexane-1,3-diamine

Product 1

HCID 178454306HCID 178454306, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1S,3R)—N1-(2-chloro-5-fluoro-pyrimidin-4-yl)cyclohexane-1,3-diamine, 70a, (0.122 g, 0.500 mmol) in CH2Cl2 (10 mL) was added tert-butyl N—(N-tert-butoxycarbonyl-C-pyrazol-1-yl-carbonimidoyl)carbamate (0.155 g, 0.500 mmol). The reaction mixture was stirred at room temperature for 2 days. The reaction mixture was concentrated in vacuo and used without further purification: 1H NMR (300 MHz, CDCl3) δ 11.51 (s, 3H), 8.29 (d, J=8.3 Hz, 3H), 7.88 (d, J=2.8 Hz, 3H), 5.01 (d, J=7.4 Hz, 3H), 4.28-4.18 (m, 4H), 2.48 (d, J=11.7 Hz, 3H), 2.12 (d, J=9.4 Hz, 3H), 1.87 (dd, J=10.3, 3.5 Hz, 3H), 1.52 (s, 24H), 1.50 (s, 25H), 1.24-1.10 (m, 8H); LCMS RT=3.97 (M+H) 487.12.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customused without further purification
  3. customLCMS RT=3.97 (M+H) 487.12

Sources & evidence

ORD record
ord-f5cc5282ba4f4d9abd7d294b29f1f5e2
Source dataset
uspto-grants-2016_05
Patent number
US09345708B2

Reaction notes

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