Ethanamine, 2,2,2-trifluoro- → HCID 86722600, compound

HRID 1503786Notes

Reaction equation

HRID 1503786 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([C:12]([OH:14])=O)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.Cl.[F:27][C:28]([F:32])([F:31])[CH2:29][NH2:30]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[F:27][C:28]([F:32])([F:31])[CH2:29][NH:30][C:12]([C:9]1([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:10][CH2:11]1)=[O:14]

Participants

6

Reactant 3

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 6883961-((tert-Butoxycarbonyl)amino)cyclopropanecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 86722600HCID 86722600, compoundYield 84.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-((tert-butoxycarbonyl)amino)cyclopropanecarboxylic acid (10.0 g, 49.7 mmol) in CH2Cl2 (80 mL) was added EDC.HCl (13.8 g, 71.8 mmol) followed by 2,2,2-trifluoroethylamine (8.21 g, 82.8 mmol) and 4-(dimethylamino)pyridine (7.31 g, 59.8 mmol). The reaction mixture was stirred at ambient temperature for 18 h, taken up in 300 mL of EtOAC, then washed with aq. 10% HCl (3×), aq. 10% K2CO3 (2×) and aq. sat. NaCl (1×). The organic phase was dried (MgSO4) and concentrated in vacuo to afford the title compound as a white solid (11.8 g, 84%): mp 166-167° C.; 1H NMR (400 MHz, DMSO-d6) rotamers δ8.43 (s, 0.3H), 8.20 (s, 0.7H), 7.41 (s, 0.7H), 7.11 (s, 0.3H), 3.84 (dt, J=9.9, 4.9 Hz, 2H), 1.38 (d, J=11.4 Hz, 9H), 1.24 (q, J=4.3 Hz, 2H), 0.92 (q, J=4.3 Hz, 2H); 19F NMR (376 MHz, DMSO-d6) δ −70.57; 13C NMR (101 MHz, DMSO-d6) rotamers δ 172.82, 155.37, 124.64 (q, J=281 Hz), 78.29, 40.18 (q, J=34 Hz), 35.43, 34.70, 28.05, 27.84, 17.28, 16.62.

Workup

  1. washwashed with aq. 10% HCl (3×), aq. 10% K2CO3 (2×) and aq. sat. NaCl (1×)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0c38567f0c514d5db0d87973e23a3ede
Source dataset
uspto-grants-2015_12
Patent number
US09212164B2

Reaction notes

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