Hydrochloric Acid → HCID 59446865, compound

HRID 1946803Notes

Reaction equation

HRID 1946803 reaction equation
[CH:1]1([CH2:4][N:5]([CH2:30][CH2:31][CH3:32])[C:6]2[N:11]=[CH:10][N:9]=[C:8]([C:12]([NH:14][C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[N:20]([CH2:24][C:25]([O:27]CC)=[O:26])[N:19]=[CH:18]4)=[O:13])[CH:7]=2)[CH2:3][CH2:2]1.[OH-].[Na+].O.Cl>C(O)C.C(Cl)Cl>[CH:1]1([CH2:4][N:5]([CH2:30][CH2:31][CH3:32])[C:6]2[N:11]=[CH:10][N:9]=[C:8]([C:12]([NH:14][C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[N:20]([CH2:24][C:25]([OH:27])=[O:26])[N:19]=[CH:18]4)=[O:13])[CH:7]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 25183071HCID 25183071, compound2×

Product 1

HCID 59446865HCID 59446865, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 2-(5-(6-((cyclopropylmethyl)(propyl)amino)pyrimidine-4-carboxamido)-1H-indazol-1-yl)acetate (Intermediate 39, 106 mg; 0.24 mmol) in ethanol (10 ml) was treated with 10% NaOH solution (5 ml). After stirring at RT for 2 hours the solvent was reduced in vacuo to one quarter of its original volume and water (20 ml) added. The mixture was acidified with dilute HCl and DCM (50 ml) added. After stirring at RT for 30 minutes the mixture was filtered through a hydrophobic frit and the solvent removed in vacuo. The solid formed was washed with water and dried to give the title compound as a pale yellow solid.

Workup

  1. additionadded
  2. additionadded
  3. stirringAfter stirring at RT for 30 minutes the mixture
  4. filtrationwas filtered through a hydrophobic frit
  5. customthe solvent removed in vacuo
  6. customThe solid formed
  7. washwas washed with water
  8. customdried

Sources & evidence

ORD record
ord-34edb459b9ce45d98c3c6d7ff04ab05a
Source dataset
uspto-grants-2013_03
Patent number
US08399448B2

Reaction notes

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