Hydrochloric Acid → HCID 57438777, compound

HRID 2233117Notes

Reaction equation

HRID 2233117 reaction equation
C([O:3][C:4](=[O:33])[C:5]([CH3:32])([CH3:31])[CH2:6][NH:7][C:8]1[N:13]=[C:12]([C:14]2[N:18]3[CH:19]=[CH:20][N:21]=[C:22]([CH3:23])[C:17]3=[N:16][C:15]=2[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[CH:11]=[CH:10][N:9]=1)C.[OH-].[Na+].Cl>CO.C(Cl)Cl.O>[F:30][C:27]1[CH:26]=[CH:25][C:24]([C:15]2[N:16]=[C:17]3[C:22]([CH3:23])=[N:21][CH:20]=[CH:19][N:18]3[C:14]=2[C:12]2[CH:11]=[CH:10][N:9]=[C:8]([NH:7][CH2:6][C:5]([CH3:32])([CH3:31])[C:4]([OH:33])=[O:3])[N:13]=2)=[CH:29][CH:28]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57438778HCID 57438778, compound

Product 1

HCID 57438777HCID 57438777, compoundYield 45.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

3-{4-[2-(4-Fluorophenyl)-8-methylimidazo[1,2-a]pyrazin-3-yl]pyrimidin-2-ylamino}-2,2-dimethyl-propionic acid ethyl ester (Example #A.9.19, 0.085 g, 0.19 mmol) was diluted in MeOH (3 mL) and treated with 2.5 M NaOH (0.36 mL, 0.9 mmol) at ambient temperature. After about 4 days, the mixture was neutralized with 1.0 M HCl (0.90 mL, 0.9 mmol) and diluted with DCM and water. The layers were separated and the aqueous layer was extracted with DCM. The combined organic layers were dried over Na2SO4, decanted, and concentrated to yield the title compound (0.036 g, 45%): LC/MS (Table 1, Method b) Rt=1.9 min; MS m/z: 421.3 (M+H)+.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with DCM
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. customdecanted
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-40b52236abbd4a4ebff279d7a3970d8d
Source dataset
uspto-grants-2010_05
Patent number
US07709468B2

Reaction notes

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