Hydrochloric Acid → (5)-4-(3-(3-Cyclopropyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin-8-yl)-8-((2,4-dimethoxybenzyl)amino)imidazo[1,5-a]pyrazin-1-yl)benzoic acid

HRID 62469Notes

Reaction equation

HRID 62469 reaction equation
[CH:1]1([C:4]2[N:8]3[CH2:9][CH2:10][CH2:11][C@@H:12]([C:13]4[N:17]5[CH:18]=[CH:19][N:20]=[C:21]([NH:22][CH2:23][C:24]6[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:25]=6[O:32][CH3:33])[C:16]5=[C:15]([C:34]5[CH:43]=[CH:42][C:37]([C:38]([O:40]C)=[O:39])=[CH:36][CH:35]=5)[N:14]=4)[C:7]3=[N:6][N:5]=2)[CH2:3][CH2:2]1.O[Li].O.Cl>C1COCC1.CO.O>[CH:1]1([C:4]2[N:8]3[CH2:9][CH2:10][CH2:11][C@@H:12]([C:13]4[N:17]5[CH:18]=[CH:19][N:20]=[C:21]([NH:22][CH2:23][C:24]6[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:25]=6[O:32][CH3:33])[C:16]5=[C:15]([C:34]5[CH:43]=[CH:42][C:37]([C:38]([OH:40])=[O:39])=[CH:36][CH:35]=5)[N:14]=4)[C:7]3=[N:6][N:5]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 118559027(5)-Methyl 4-(3-(3-cyclopropyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridine-8-yl)-8-((2,4-dimethoxybenzyl)amino)imidazo[1,5-a]pyrazin-1-yl)benzoate

Product 1

HCID 90303981(5)-4-(3-(3-Cyclopropyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin-8-yl)-8-((2,4-dimethoxybenzyl)amino)imidazo[1,5-a]pyrazin-1-yl)benzoic acidYield 45.1%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of (S)-methyl 4-(3-(3-cyclopropyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridine-8-yl)-8-((2,4-dimethoxybenzyl)amino)imidazo[1,5-a]pyrazin-1-yl)benzoate (300 mg, 0.51 mmol) in THF/MeOH/H2O (3 mL/3 mL/1 mL) was added LiOH.H2O (109 mg, 2.6 mmol). The mixture was stirred at RT overnight. After the reaction was completed, the reaction mixture was acidified by 2M HCl to pH=5˜6 and extracted with EA and water. The organic layer was dried and concentrated to give (S)-4-(3-(3-cyclopropyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin-8-yl)-8-((2,4-dimethoxybenzyl)amino)imidazo[1,5-a]pyrazin-1-yl)benzoic acid (130 mg, yield 45%).

Workup

  1. extractionextracted with EA and water
  2. customThe organic layer was dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a51e757768304c0abb01772d61b7b539
Source dataset
uspto-grants-2016_09
Patent number
US09446130B2

Reaction notes

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