Hydrochloric Acid → HCID 90182691, compound

HRID 919305Notes

Reaction equation

HRID 919305 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[CH2:11][C@@H:10]2[CH2:12][O:13][C:14]2[C:19]([C:20]3[CH:25]=[CH:24][N:23]([CH2:26][C:27]([O:29]C)=[O:28])[C:22](=[O:31])[CH:21]=3)=[CH:18][N:17]=[C:16]([CH3:32])[N:15]=2)=[N:7][CH:8]=1.[Li+].[OH-].Cl>O1CCCC1.CO.O.[Cl-].[Na+].O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[CH2:11][C@@H:10]2[CH2:12][O:13][C:14]2[C:19]([C:20]3[CH:25]=[CH:24][N:23]([CH2:26][C:27]([OH:29])=[O:28])[C:22](=[O:31])[CH:21]=3)=[CH:18][N:17]=[C:16]([CH3:32])[N:15]=2)=[N:7][CH:8]=1

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 76073011HCID 76073011, compound

Product 1

HCID 90182691HCID 90182691, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of methyl 2-(4-(4-(((1S,2S)-2-(5-methoxypyridin-2-yl)cyclopropyl)methoxy)-2-methylpyrimidin-5-yl)-2-oxopyridin-1(2H)-yl)acetate (Example 56, 30 mg, 0.069 mmol) in tetrahydrofuran (1 ml), methanol (1 ml) and H2O (1 ml) was added LiOH (8.3 mg, 0.3 mmol). The reaction mixture was stirred at ambient temperature for 16 hours. To the reaction mixture was added 5 ml of brine and the pH was adjusted to 3 with 1N HCl to provide a white precipitate which was filtered and dried to provide the title compound as a white solid. LC/MS: m/z=423.1 [M+H]+; 1H NMR (400 MHz, MeOD) δ 8.50 (s, 1 H), 8.05 (s, 1 H), 7.62 (d, 1 H), 7.56 (dd, 1 H), 7.32 (dd, 1 H), 6.83 (d, 1 H), 6.68 (dd, 1 H), 4.74 (d, 2 H), 4.59-4.63 (m, 1 H), 4.44-4.49 (m, 1H), 3.84 (s, 3 H), 2.63 (s, 3 H), 2.15-2.19 (m, 1 H), 1.81-1.83 (m, 1 H), 1.24-1.29 (m, 1 H), 1.09-1.14 (m, 1 H).

Workup

  1. customto provide a white precipitate which
  2. filtrationwas filtered
  3. customdried

Sources & evidence

ORD record
ord-b71e67b05d3e4925a3eb9e7b861b069b
Source dataset
uspto-grants-2016_03
Patent number
US09273033B2

Reaction notes

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