Water → HCID 52951272, compound

HRID 508602Notes

Reaction equation

HRID 508602 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:4]([C:13]2[CH:18]=[CH:17][C:16]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)[N:3]=1.[F:23][C:24]([F:35])([F:34])[C:25]1[CH:26]=[C:27]([N:31]=[C:32]=[O:33])[CH:28]=[CH:29][CH:30]=1.C(N(CC)CC)C.O>CN(C=O)C>[C:7]1([C:5]2[N:4]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([NH2:22])(=[O:20])=[O:21])=[CH:15][CH:14]=3)[N:3]=[C:2]([NH:1][C:32]([NH:31][C:27]3[CH:28]=[CH:29][CH:30]=[C:25]([C:24]([F:23])([F:34])[F:35])[CH:26]=3)=[O:33])[CH:6]=2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 52951166HCID 52951166, compound

Product 1

HCID 52951272HCID 52951272, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of amine 6 (0.1 g, 0.32 mmol) in 5 mL of DMF was added 3-(trifluoromethyl)phenyl isocyanate (0.12 g, 0.62 mmol) followed by triethylamine (0.05 mL, 0.32 mmol) at 0° C. The reaction mixture was warmed up to room temperature and stirred overnight. The reaction mixture was poured into water, and the resulting precipitates were collected and washed with water. The crude product was purified by column chromatography by dry loading method to give the titled compound (0.13 g, 81% yield). mp 195.1-197.0° C. 1H NMR (300 MHz, DMSO-d6): δ 9.48 (s, 1H), 9.21 (s, 1H), 8.07 (s, 1H), 7.80 (d, J=9 Hz, 2H), 7.61-7.26 (m, 12H), 6.81 (s, 1H). MS (ESI) m/z: 502.12 (M+H+). Anal. Calcd for C23H18F3N5O3S.0.36CH4O: C, 54.69; H, 3.82; N, 13.65. Found: C, 54.69; H, 3.70; N, 13.44.

Workup

  1. customthe resulting precipitates
  2. customwere collected
  3. washwashed with water
  4. customThe crude product was purified by column chromatography
  5. customby dry loading method

Sources & evidence

ORD record
ord-5c682b22891e4bd895909b27dd4c393a
Source dataset
uspto-grants-2015_08
Patent number
US09096532B2

Reaction notes

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