2-Bromophenyl isocyanate → HCID 9910487, compound

HRID 2109518Notes

Reaction equation

HRID 2109518 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:11][CH:10]([NH2:12])[CH2:9]2)[CH:5]=[C:4]([C:13]([F:16])([F:15])[F:14])[CH:3]=1.[Br:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N:24]=[C:25]=[O:26]>ClCCl>[Br:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[NH:24][C:25]([NH:12][CH:10]1[CH2:11][N:8]([C:6]2[CH:5]=[C:4]([C:13]([F:14])([F:16])[F:15])[CH:3]=[C:2]([CH3:1])[N:7]=2)[CH2:9]1)=[O:26]

Participants

4

Reactant 2

HCID 1370972-Bromophenyl isocyanateHCID 10443877HCID 10443877, compound

Product 1

HCID 9910487HCID 9910487, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(6-methyl-4-trifluoromethylpyridin-2-yl)azetidin-3-ylamine, D12 (100 mg, 0.432 mM) and 2-bromophenyl isocyanate (86 mg, 0.432 mM) in dichloromethane (5 ml) was kept at room temperature overnight. The resultant solid was removed by centrifugation, washed with diethyl ether and dried in vacuo, to give the title compound as a colourless solid, (119 mg, 64%). MH+ 429 and 431; 1H NMR (250 MHz, d6DMSO) δ: 2.39 (3H, s), 3.75-3.88 (2H, dd), 4.30 (2H, t), 4.50-4.66 (1H, m), 6.48 (1H, s), 6.78 (1H,s), 6.92 (1H, m), 7.28 (1H, m), 7.57 (1H, dd), 7.76 (1H, d), 7.86 (1H, s), and 8.04 (1H, dd).

Workup

  1. customThe resultant solid was removed by centrifugation
  2. washwashed with diethyl ether
  3. customdried in vacuo

Sources & evidence

ORD record
ord-1dd1ea03648b46a6ab78e078af19cfca
Source dataset
uspto-grants-2009_04
Patent number
US07514562B2

Reaction notes

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