Hydrochloric Acid → 4-{4-[4-(4-Fluoro-3-trifluoromethyl-phenyl)-3-methyl-1H-imidazol-2-yl]-piperidin-1-yl}-1H-pyrazolo[3,4-d]pyrimidine hydrochloride

HRID 2194480Notes

Reaction equation

HRID 2194480 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([CH:15]3[CH2:20][CH2:19][N:18]([C:21]4[N:26]=[CH:25][N:24]=[C:23]5[NH:27][N:28]=[CH:29][C:22]=45)[CH2:17][CH2:16]3)[N:12](C)[CH:13]=2)=[CH:5][C:4]=1[C:30]([F:33])([F:32])[F:31].[Cl:34][CH2:35]Cl>>[ClH:34].[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]([CH3:35])[CH:11]([CH:15]3[CH2:16][CH2:17][N:18]([C:21]4[N:26]=[CH:25][N:24]=[C:23]5[NH:27][N:28]=[CH:29][C:22]=45)[CH2:19][CH2:20]3)[NH:12][CH:13]=2)=[CH:5][C:4]=1[C:30]([F:33])([F:32])[F:31]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 25118925Ly-2584702

Product 1

HCID 666499164-{4-[4-(4-Fluoro-3-trifluoromethyl-phenyl)-3-methyl-1H-imidazol-2-yl]-piperidin-1-yl}-1H-pyrazolo[3,4-d]pyrimidine hydrochlorideYield 98.47%

Procedure

Add hydrogen chloride (1.1 equiv; 18.52 mmoles; 4.63 mL) to a suspension of 4-{4-[4-(4-fluoro-3-trifluoromethyl-phenyl)-1-methyl-1H-imidazol-2-yl]-piperidin-1-yl}-1H-pyrazolo[3,4-d]pyrimidine (7.5 g; 1.00 equiv; 16.84 mmoles) in dichloromethane (50 mL), and stir the mixture for 1 hour at RT. Remove the solvent in vacuo, and triturate the crude in MTBE for 1 hour. Filter the solid and dry in vacuo overnight to give 4-{4-[4-(4-Fluoro-3-trifluoromethyl-phenyl)-3-methyl-1H-imidazol-2-yl]-piperidin-1-yl}-1H-pyrazolo[3,4-d]pyrimidine hydrochloride (7.99 g; 16.58 mmoles; 98.47% yield) as a white solid. 1H-NMR (300 MHz, DMSO): 614.01-13.99 (m, 1H), 8.57-8.54 (m, 2H), 8.26-8.19 (m, 3H), 7.72-7.63 (m, 1H), 5.23-5.20 (m, 2H), 3.89 (s, 3H), 3.41 (m, 2H), 2.15-2.07 (m, 3H), 1.10 (s, 2H).

Workup

  1. customRemove the solvent in vacuo
  2. customtriturate the crude in MTBE for 1 hour
  3. filtrationFilter the solid
  4. customdry in vacuo overnight

Sources & evidence

ORD record
ord-4d6e40018bd64603897831f6c7a81d77
Source dataset
uspto-grants-2012_12
Patent number
US08334293B2

Reaction notes

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