p-(Trifluoromethoxy)phenyl isocyanate → HCID 72204617, compound

HRID 711301Notes

Reaction equation

HRID 711301 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:7]=[C:8]([CH:15]=[CH:16][CH:17]=1)[CH2:9][NH:10][CH:11]([C:13]#[CH:14])[CH3:12].[N:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=1)=[C:19]=[O:20]>C(Cl)Cl>[CH3:12][CH:11]([N:10]([CH2:9][C:8]1[CH:15]=[CH:16][CH:17]=[C:6]([C:2]2[S:1][CH:5]=[CH:4][N:3]=2)[CH:7]=1)[C:19]([NH:18][C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]([F:29])([F:30])[F:31])=[CH:23][CH:22]=1)=[O:20])[C:13]#[CH:14]

Participants

4

Reactant 2

HCID 92298p-(Trifluoromethoxy)phenyl isocyanateHCID 90023225HCID 90023225, compound

Product 1

HCID 72204617HCID 72204617, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the crude N-[3-(1,3-thiazol-2-yl)benzyl]but-3-yn-2-amine (25 mg, 0.10 mmol) in 1 mL CH2Cl2 was added 1-isocyanato-4-(trifluoromethoxy)benzene (31 mg, 0.16 mmol). The reaction was allowed to stir at ambient temperature for 5 min, concentrated, and purified on a Waters reverse phase preparatory instrument to give 1-(1-methylprop-2-yn-1-yl)-1-[3-(1,3-thiazol-2-yl)benzyl]-3-[4-(trifluoromethoxy)phenyl]urea. 1H NMR (399 MHz, CD3 OD): δ 7.96 (s, 1 H); 7.84 (d, J=10.5 Hz, 2 H); 7.60 (d, J=3.5 Hz, 1 H); 7.47 (d, J=4.9 Hz, 2H); 7.38 (d, J=8.8 Hz, 2 H); 7.14 (d, J=8.6 Hz, 2 H); 5.39 (d, J=7.7 Hz, 1 H); 4.94-4.76 (m, 2 H) 2.83-2.81 (m, 1 H); 1.42 (d, J=7.1 Hz, 3 H). LCMS [M+H]+=446.2.

Workup

  1. concentrationconcentrated
  2. custompurified on a Waters reverse phase preparatory instrument

Sources & evidence

ORD record
ord-3f52946eb09d47c081e2b59d998f83d4
Source dataset
uspto-grants-2015_11
Patent number
US09181261B2

Reaction notes

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