Phenyl isocyanate → 1-(2-Fluoro-4-(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazine-1-carbonyl)phenyl)-3-phenylurea

HRID 1807752Notes

Reaction equation

HRID 1807752 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([OH:32])([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)=[O:9])=[CH:4][C:3]=1[F:33].[N:34]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[C:35]=[O:36]>>[F:33][C:3]1[CH:4]=[C:5]([C:8]([N:10]2[CH2:11][CH2:12][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([OH:32])([C:24]([F:25])([F:26])[F:27])[C:28]([F:30])([F:31])[F:29])=[CH:19][CH:18]=3)[CH2:14][CH2:15]2)=[O:9])[CH:6]=[CH:7][C:2]=1[NH:1][C:35]([NH:34][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:36]

Participants

3

Reactant 2

HCID 7672Phenyl isocyanate2×HCID 86638550(4-Amino-3-fluorophenyl)(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazin-1-yl)methanone

Product 1

HCID 591758691-(2-Fluoro-4-(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazine-1-carbonyl)phenyl)-3-phenylureaYield 56.8%

Conditions

Temperature
100 °C

Procedure

(4-Amino-3-fluorophenyl)(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazin-1-yl)methanone (0.209 mmol, 0.1 g) and isocyanatobenzene (0.229 mmol, 0.025 mL, 0.027 g) were combined and heated in the microwave at 100° C. for 10 minutes. Further isocyanatobenzene (0.229 mmol, 0.025 mL, 0.027 g) was added and the reaction heated in the microwave for a further 10 minutes at 100° C. The reaction mixture was concentrated under reduced pressure and purified by acidic preparative HPLC to afford the title compound (71 mg). MS (ESI) m/z 599.0 [M+H]+

Workup

  1. temperaturethe reaction heated in the microwave for a further 10 minutes at 100° C
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. custompurified by acidic preparative HPLC

Sources & evidence

ORD record
ord-03a5683b562948e3a3185c5ebeba6751
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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