Diisopropylethylamine → HCID 66649846, compound

HRID 419740Notes

Reaction equation

HRID 419740 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]([N:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)=[N:10][CH:9]=2)=[CH:4][C:3]=1[C:19]([F:22])([F:21])[F:20].Cl[C:24]1[N:29]=[CH:28][N:27]=[C:26]2[NH:30][N:31]=[CH:32][C:25]=12.C(N(C(C)C)CC)(C)C>C(O)(C)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]([N:13]3[CH2:14][CH2:15][N:16]([C:24]4[N:29]=[CH:28][N:27]=[C:26]5[NH:30][N:31]=[CH:32][C:25]=45)[CH2:17][CH2:18]3)=[N:10][CH:9]=2)=[CH:4][C:3]=1[C:19]([F:22])([F:20])[F:21]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2210954-Chloro-1H-pyrazolo[3,4-d]pyrimidineHCID 66649874HCID 66649874, compound

Product 1

HCID 66649846HCID 66649846, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Combine 1-[5-(4-Fluoro-3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-piperazine (195 mg, 1.00 equiv; 0.620 mmoles); 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine (1.00 equiv; 0.620 mmoles; 96 mg); isopropyl alcohol (3 mL); diisopropylethylamine (1 mL) and heat in a microwave reactor at 80° C. for 60 min. Evaporate the reaction mixture and purify on silica gel with 5% MeOH/DCM. Combine the fractions to give 213.2 mg (0.494 mmol, 80%) of 4-{4-[5-(4-Fluoro-3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-piperazin-1-yl}-1H-pyrazolo[3,4-d]pyrimidine. Dissolve the free base in DCM/MeOH and add 1.0 eq 1M HCl in ether. Concentrate the mixture to give 237.2 mg 4-{4-[5-(4-Fluoro-3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-piperazin-1-yl}-1H-pyrazolo[3,4-d]pyrimidine hydrochloride.

Workup

  1. customEvaporate the reaction mixture
  2. custompurify on silica gel with 5% MeOH/DCM

Sources & evidence

ORD record
ord-4281d18df5944fddb373ca3aefe40ff4
Source dataset
uspto-grants-2012_01
Patent number
US08093383B2

Reaction notes

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