Methanol → HCID 68115306, compound

HRID 525054Notes

Reaction equation

HRID 525054 reaction equation
[CH3:1][N:2]([CH2:22][C:23]1[CH:32]=[CH:31][C:26]([C:27]([O:29]C)=[O:28])=[CH:25][CH:24]=1)[CH:3]1[CH2:8][CH2:7][CH:6]([NH:9][C:10]2[C:21]3[C:20]4[CH2:19][CH2:18][CH2:17][C:16]=4[S:15][C:14]=3[N:13]=[CH:12][N:11]=2)[CH2:5][CH2:4]1.CO.[OH-].[Na+]>O>[CH3:1][N:2]([CH2:22][C:23]1[CH:32]=[CH:31][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=1)[CH:3]1[CH2:4][CH2:5][CH:6]([NH:9][C:10]2[C:21]3[C:20]4[CH2:19][CH2:18][CH2:17][C:16]=4[S:15][C:14]=3[N:13]=[CH:12][N:11]=2)[CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 68115404HCID 68115404, compound

Product 1

HCID 68115306HCID 68115306, compoundYield 206.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of methyl 4-([methyl[4-([7-thia-9,11-diazatricyclo[6.4.0.0^[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]amino)cyclohexyl]amino]methyl)benzoate (500 mg, 1.11 mmol, 1.00 equiv), methanol (20 mL), sodium hydroxide (89 mg, 2.23 mmol, 2.00 equiv) and water (2 mL) was stirred for 2 h at 50° C. in an oil bath. The resulting mixture was concentrated under vacuum. The pH value of the solution was adjusted to 1 with hydrogen chloride (12 mol/L). The resulting mixture was concentrated under vacuum to yield 1 g of crude 4-([methyl[4-([7-thia-9,11-diazatricyclo[6.4.0.0^[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]amino)cyclohexyl]amino]methyl)benzoic acid as a yellow solid. The crude product was used in the next step without further purification. MS: m/z 437 (M+H)+.

Workup

  1. concentrationThe resulting mixture was concentrated under vacuum
  2. concentrationThe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-fe8a61857194477297143b1bc04da74f
Source dataset
uspto-grants-2016_05
Patent number
US09340554B2

Reaction notes

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