(3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methanamine → HCID 70816570, compound

HRID 1842870Notes

Reaction equation

HRID 1842870 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([CH2:10][NH2:11])[N:7]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[F:19][C:20]1[CH:21]=[C:22]([NH:31][C:32](=O)[O:33]C2C=CC=CC=2)[CH:23]=[CH:24][C:25]=1[O:26][CH2:27][CH2:28][O:29][CH3:30]>CC#N>[C:1]([C:5]1[CH:9]=[C:8]([CH2:10][NH:11][C:32]([NH:31][C:22]2[CH:23]=[CH:24][C:25]([O:26][CH2:27][CH2:28][O:29][CH3:30])=[C:20]([F:19])[CH:21]=2)=[O:33])[N:7]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 58093530(3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methanamineHCID 86672139HCID 86672139, compound

Product 1

HCID 70816570HCID 70816570, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of (3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methanamine (synthesis described for example A18) (81 mg, 0.31 mmol, 1.0 eq.) in MeCN (7 mL) was added TEA (0.17 mL, 1.2 mmol, 4.0 eq.) followed by phenyl 3-fluoro-4-(2-methoxyethoxy)phenylcarbamate (95 mg, 0.31 mmol, 1.0 eq.) at RT and stirred at reflux for 16 h. The solvent was evaporated under vacuum. The crude product obtained was purified by column chromatography (eluent EtOAc/n-hexane 1:1) to yield example A17 (121 mg; 83%).

Workup

  1. temperatureat reflux for 16 h
  2. customThe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-8a5ee99505db4095aa52c0f161abdac2
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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