Propylamine → 1,1,1-Trifluoro-3-{[1-(4-fluorophenyl)-6-methyl-1H-indazol-4-yl]amino}-2-[(propylamino)methyl]-2-propanol

HRID 551434Notes

Reaction equation

HRID 551434 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[CH:15]=[C:14]([CH3:17])[CH:13]=[C:12]([NH:18][CH2:19][C:20]4([C:23]([F:26])([F:25])[F:24])[CH2:22][O:21]4)[C:11]=3[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[CH2:27]([NH2:30])[CH2:28][CH3:29]>ClCCl>[F:24][C:23]([F:26])([F:25])[C:20]([CH2:22][NH:30][CH2:27][CH2:28][CH3:29])([OH:21])[CH2:19][NH:18][C:12]1[CH:13]=[C:14]([CH3:17])[CH:15]=[C:16]2[C:11]=1[CH:10]=[N:9][N:8]2[C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 7852PropylamineHCID 24938054HCID 24938054, compound

Product 1

HCID 593241651,1,1-Trifluoro-3-{[1-(4-fluorophenyl)-6-methyl-1H-indazol-4-yl]amino}-2-[(propylamino)methyl]-2-propanolYield 24.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-fluorophenyl)-6-methyl-N-{[2-(trifluoromethyl)-2-oxiranyl]methyl}-1H-indazol-4-amine (1.4 g, 3.84 mmol) in dichloromethane (50 ml) was added n-propylamine (20 ml, 243 mmol). The reaction was stirred at room temperature overnight and then evaporated in vacuo. The crude product was purified on a 70 g silica Bond Elut cartridge using a 0-50% ethyl acetate in dichloromethane gradient over 60 minutes to give the title compound (0.4 g).

Workup

  1. customevaporated in vacuo
  2. customThe crude product was purified on a 70 g silica Bond Elut cartridge
  3. customover 60 minutes

Sources & evidence

ORD record
ord-f23864f79fd3425bafe1c58b521b25d1
Source dataset
uspto-grants-2011_05
Patent number
US07947727B2

Reaction notes

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