Methanol → Sodium 4-[6-(cyclopentyloxycarbonyl)aminoindazol-1-ylmethyl]-3-methoxybenzoate

HRID 358749Notes

Reaction equation

HRID 358749 reaction equation
[CH:1]1([O:6][C:7]([NH:9][C:10]2[CH:18]=[C:17]3[C:13]([CH:14]=[N:15][N:16]3[CH2:19][C:20]3[CH:28]=[CH:27][C:23]([C:24]([OH:26])=[O:25])=[CH:22][C:21]=3[O:29][CH3:30])=[CH:12][CH:11]=2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.CO.[OH-].[Na+:34]>C(Cl)Cl>[CH:1]1([O:6][C:7]([NH:9][C:10]2[CH:18]=[C:17]3[C:13]([CH:14]=[N:15][N:16]3[CH2:19][C:20]3[CH:28]=[CH:27][C:23]([C:24]([O-:26])=[O:25])=[CH:22][C:21]=3[O:29][CH3:30])=[CH:12][CH:11]=2)=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5]1.[Na+:34]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 147087514-[6-(Cyclopentyloxycarbonyl)aminoindazol-1-ylmethyl]-3-methoxybenzoic acid

Product 1

HCID 23710210Sodium 4-[6-(cyclopentyloxycarbonyl)aminoindazol-1-ylmethyl]-3-methoxybenzoateYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 306 mg. 4-[6-(cyclopentyloxycarbonyl)aminoindazol-1-ylmethyl]-3-methoxybenzoic acid in 4 ml. methanol and 6 ml. methylene chloride was treated with 0.75 ml. of 1 M sodium hydroxide solution. After 15 minutes the mixture was evaporated and the residue was recrystallised from ether/methylene chloride/methanol to give sodium 4-[6-(cyclopentyloxycarbonyl)aminoindazol-1-ylmethyl]-3-methoxybenzoate in 78% yield as a solid, m.p. >280° C. (d); microanalysis, found: C,59.80; H,5.06; N,9.20%; C22H22H3O5Na.0.5H2O requires C, 59.99; H,5.26; N,9.54%.

Workup

  1. additionA mixture of 306 mg
  2. customAfter 15 minutes the mixture was evaporated
  3. customthe residue was recrystallised from ether/methylene chloride/methanol

Sources & evidence

ORD record
ord-c9613137f61246e1bfc0786f7875d0e1
Source dataset
uspto-grants-1991_03
Patent number
US04997844

Reaction notes

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