Lithium Hydroxide → HCID 10183034, compound

HRID 1373801Notes

Reaction equation

HRID 1373801 reaction equation
[CH:1]1([NH:6][C:7]2[N:12]=[C:11]([C:13]3[C:14]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)=[N:15][N:16]4[C:21]([NH:22][CH2:23][C:24]([O:26]C)=[O:25])=[CH:20][CH:19]=[CH:18][C:17]=34)[CH:10]=[C:9]([CH3:35])[N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Li+]>O1CCCC1.CO>[CH:1]1([NH:6][C:7]2[N:12]=[C:11]([C:13]3[C:14]([C:28]4[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=4)=[N:15][N:16]4[C:21]([NH:22][CH2:23][C:24]([OH:26])=[O:25])=[CH:20][CH:19]=[CH:18][C:17]=34)[CH:10]=[C:9]([CH3:35])[N:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 10277116HCID 10277116, compound

Product 1

HCID 10183034HCID 10183034, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a room temperature solution of methyl {[3-[2-(cyclopentylamino)-6-methyl-4-pyrimidinyl]-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-7-yl]amino}acetate (76 mg, 0.16 mmol) in tetrahydrofuran (3 mL) and methanol (1 mL) was added lithium hydroxide (1 mL, 1.0 M in water, 1 mmol). The resultant mixture was stirred at room temperature for 24 hours then concentrated in vacuo. The residue was suspended in ether and acidified with aqueous hydrochloric acid (4N). The solids were filtered and azeotroped twice with methanol in vacuo to provide the hydrochloride salt of {[3-[2-(cyclopentylamino)-6-methyl-4-pyrimidinyl]-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-7-yl]amino}acetic acid (70 mg, 95%) as a yellow solid.1H NMR (CDCl3) δ 7.72–7.34 (m, 7H), 6.40–6.26 (m, 2H), 4.17–4.04 (m, 3H), 2.20 (s, 3H), 1.88 (m, 2H), 1.69 (m, 2H), 1.54 (m, 4H); 19F NMR (CDCl3) δ −112.96; MS m/z 461 (M+1).

Workup

  1. concentrationthen concentrated in vacuo
  2. filtrationThe solids were filtered
  3. customazeotroped twice with methanol in vacuo

Sources & evidence

ORD record
ord-545f9ec0c71a445db4fb81a97f556125
Source dataset
uspto-grants-2007_01
Patent number
US07163940B2

Reaction notes

Loading…