Lithium Hydroxide → HCID 86677741, compound

HRID 1499817Notes

Reaction equation

HRID 1499817 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:12]([C:14]3[C:15]([O:32][CH3:33])=[C:16]([CH:22]4[CH2:25][N:24]([C@H:26]([CH3:31])[C:27]([O:29]C)=[O:28])[CH2:23]4)[C:17]([CH3:21])=[C:18]([Cl:20])[CH:19]=3)[CH3:13])[N:9]=[C:10]([CH3:11])[C:3]=12.[OH-].[Li+]>C(#N)C.O.C(OCC)(=O)C.Cl>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:12]([C:14]3[C:15]([O:32][CH3:33])=[C:16]([CH:22]4[CH2:25][N:24]([C@H:26]([CH3:31])[C:27]([OH:29])=[O:28])[CH2:23]4)[C:17]([CH3:21])=[C:18]([Cl:20])[CH:19]=3)[CH3:13])[N:9]=[C:10]([CH3:11])[C:3]=12

Participants

7

Reactant 2

HCID 3939Lithium HydroxideHCID 86677740HCID 86677740, compound2×

Product 1

HCID 86677741HCID 86677741, compoundYield 83%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl (2R)-2-(3-{3-[1-(4-amino-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-5-chloro-2-methoxy-6-methylphenyl}azetidin-1-yl)propanoate (chiral intermediate from example 156 step 2) (13 mg, 0.027 mmol) in acetonitrile (0.6 mL) and water (0.2 mL) was added lithium hydroxide (2.4 mg, 0.10 mmol). The reaction mixture was stirred at room temperature overnight. The reaction solution was diluted with ethyl acetate and 1 M HCl solution. The organic layer was separated and dried over Na2SO4, filtered and concentrated to give the desired product (10.2 mg, 83%). LCMS calculated for C22H28ClN6O3 (M+H)+: m/z=459.2; Found: 459.1.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d806bd600da7420cac68a389f882397e
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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