Hydrochloric Acid → HCID 59446865, compound

HRID 1746783Notes

Reaction equation

HRID 1746783 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-305dda91898947d998e6cde1340caf5c
Source dataset
uspto-grants-2015_10
Patent number
US09150519B2

Reaction notes

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