Hydrochloric Acid → HCID 178434171, compound

HRID 1913236Notes

Reaction equation

[CH3:1][C:2]1([C:34]([O:36]CC)=[O:35])[CH2:7][CH2:6][CH:5]([CH2:8][C:9]2[C:14]3[C:15]([CH3:18])=[N:16][NH:17][C:13]=3[N:12]3[N:19]=[CH:20][C:21]([C:22]4[CH:23]=[N:24][C:25]([C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)=[CH:26][CH:27]=4)=[C:11]3[N:10]=2)[CH2:4][CH2:3]1.C1COCC1.O[Li].O.Cl>O>[CH3:1][C:2]1([C:34]([OH:36])=[O:35])[CH2:3][CH2:4][CH:5]([CH2:8][C:9]2[C:14]3[C:15]([CH3:18])=[N:16][NH:17][C:13]=3[N:12]3[N:19]=[CH:20][C:21]([C:22]4[CH:23]=[N:24][C:25]([C:28]5[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=5)=[CH:26][CH:27]=4)=[C:11]3[N:10]=2)[CH2:6][CH2:7]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a 20 mL scintillation vial was charged ethyl 1-methyl-4-((3-methyl-6-(6-phenylpyridin-3-yl)-1H-dipyrazolo[1,5-a:4′,3′-e]pyrimidin-4-yl)methyl)cyclohexanecarboxylate (Int-6c, 0.03 mmol). To this residue was added 2:1 THF:H2O (1.5 mL) and LiOH.H2O (20 mg). The resulting solution was stirred at 80° C. for 4 days. After 4 days, the reaction was brought to pH 3 with 1N HCl(aq). The reaction was reduced in vacuo and the residue was purified via reverse-phase preparatory HPLC to 1-methyl-4-((3-methyl-6-(6-phenylpyridin-3-yl)-1H-dipyrazolo[1,5-a:4′,3′-e]pyrimidin-4-yl)methyl)cyclohexanecarboxylic acid (3). (M+H=481.27, retention time=4.01 min).

Workup

waitAfter 4 days
customthe residue was purified via reverse-phase preparatory HPLC to 1-methyl-4-((3-methyl-6-(6-phenylpyridin-3-yl)-1H-dipyrazolo[1,5-a:4′,3′-e]pyrimidin-4-yl)methyl)cyclohexanecarboxylic acid (3)

Sources & evidence

ORD record: ord-74e4e0565f894515924244fe0f3481ec
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609675B2

Reaction notes

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