(1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine → 1-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-3-(3-fluoro-4-(hydroxymethyl)phenyl)urea

HRID 1842881Notes

Reaction equation

HRID 1842881 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]([CH2:13][NH2:14])=[CH:11][C:10]([C:15]([F:18])([F:17])[F:16])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[F:19][C:20]1[CH:21]=[C:22]([NH:28][C:29](=O)[O:30]C2C=CC=CC=2)[CH:23]=[CH:24][C:25]=1[CH2:26][OH:27]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]([CH2:13][NH:14][C:29]([NH:28][C:22]3[CH:23]=[CH:24][C:25]([CH2:26][OH:27])=[C:20]([F:19])[CH:21]=3)=[O:30])=[CH:11][C:10]([C:15]([F:16])([F:17])[F:18])=[N:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 66644230(1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamineHCID 86672140Phenyl (3-fluoro-4-(hydroxymethyl)phenyl)carbamate

Product 1

HCID 708160761-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-3-(3-fluoro-4-(hydroxymethyl)phenyl)ureaYield 57.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine (100 mg, 0.316 mmol, 1.0 eq.) in DCM (2.0 mL) was added TEA (0.07 mL, 0.632 mmol, 3.0 eq) followed by phenyl 3-fluoro-4-(hydroxymethyl)phenylcarbamate (82.4 mg, 0.316 mmol, 1.0 eq.) at RT and stirred for 16 h. After completion of the reaction, a solid precipitate was filtered and washed with DCM (2 mL) followed by n-pentane (5 mL) and dried to get 1-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-3-(3-fluoro-4-(hydroxymethyl)phenyl)urea (compound A59) (80 mg; 47%, white solid; TLC system: EtOAc/PE (3:2); Rf: 0.2).

Workup

  1. customAfter completion of the reaction
  2. filtrationa solid precipitate was filtered
  3. washwashed with DCM (2 mL)
  4. customdried

Sources & evidence

ORD record
ord-a1e677e5cef44302b52c6a68246e6d43
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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