Hydrochloric Acid → HCID 22346802, compound

HRID 897710Notes

Reaction equation

HRID 897710 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:29]3[CH2:34][CH2:33][N:32](C(OC(C)(C)C)=O)[CH2:31][CH2:30]3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]4[O:19][C:20]5[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:21]=5[N:22]=4)=[CH:13][CH:12]=3)[C:3]=12.[ClH:42]>CC(C)=O>[ClH:42].[ClH:42].[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)[N:9]=[C:10]([C:11]3[CH:12]=[CH:13][C:14]([NH:17][C:18]4[O:19][C:20]5[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:21]=5[N:22]=4)=[CH:15][CH:16]=3)[C:3]=12

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22346764HCID 22346764, compound

Product 1

HCID 22346802HCID 22346802, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
45 °C

Procedure

tert-Butyl 4-(4-amino-3-{4-[(5,7-dimethyl-1,3-benzoxazol-2-yl)amino]phenyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-piperidinecarboxylate (142 mg, 0.256 mmol) was dissolved in acetone (7 mL) and 6N aqueous hydrochloric acid (1.4 mL). The reaction was then heated at 45° C. which yielded a precipitate. After 2.5 hours, the precipitate was collected by vacuum filtration, washed with a minimal amount of acetone and dried on the lyophilizer to N2-{4-[4-amino-1-(4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]phenyl}-5,7-dimethyl-1,3-benzoxazol-2-amine dihydrochloride as an orange solid (130 mg, 96%); -HPLC 10.436 min, 96% purity (5% to 85% acetonitrile/0.1M aqueous ammonium acetate, buffered to pH 4.5, over 20 min at 1 mL/min; λ=254 nm; Deltapak C18, 300 Å, 5 μm, 150×3.9 mm column); m/z (MH+)=455.3.

Workup

  1. customyielded a precipitate
  2. filtrationthe precipitate was collected by vacuum filtration
  3. washwashed with a minimal amount of acetone
  4. dry with materialdried on the lyophilizer to N2-{4-[4-amino-1-(4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]phenyl}-5,7-dimethyl-1,3-benzoxazol-2-amine dihydrochloride as an orange solid (130 mg, 96%)
  5. custom-HPLC 10.436 min, 96% purity (5% to 85% acetonitrile/0.1M aqueous ammonium acetate, buffered to pH 4.5, over 20 min at 1 mL/min; λ=254 nm; Deltapak C18, 300 Å, 5 μm, 150×3.9 mm column)

Sources & evidence

ORD record
ord-55d99298423e4cf4af094c5ce622b63e
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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