Sodium Hydroxide → Sodium 4-{4-[4-(3-methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylate

HRID 237430

Reaction equation

HRID 237430 reaction equation
[OH-].[Na+:2].C[O:4][C:5]([CH:7]1[CH2:12][CH2:11][CH:10]([NH:13][C:14]2[N:19]=[C:18]([N:20]3[C:28]4[C:23](=[C:24]([O:29][CH2:30][CH2:31][CH2:32][S:33]([CH3:36])(=[O:35])=[O:34])[CH:25]=[CH:26][CH:27]=4)[CH:22]=[CH:21]3)[CH:17]=[CH:16][N:15]=2)[CH2:9][CH2:8]1)=[O:6]>O.CC(O)C>[CH3:36][S:33]([CH2:32][CH2:31][CH2:30][O:29][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]2[C:23]=1[CH:22]=[CH:21][N:20]2[C:18]1[CH:17]=[CH:16][N:15]=[C:14]([NH:13][CH:10]2[CH2:11][CH2:12][CH:7]([C:5]([O-:6])=[O:4])[CH2:8][CH2:9]2)[N:19]=1)(=[O:35])=[O:34].[Na+:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 580170934-{4-[4-(3-Methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylic acid methyl ester

Product 1

HCID 86659980Sodium 4-{4-[4-(3-methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylateYield 96.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
82 °C

Procedure

A 50% (w/w) aqueous solution of NaOH in H2O (198.95 g) was added to 4-{4-[4-(3-Methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylic acid methyl ester (830.0 g) in IPA (7.5 L) and the mixture allowed to stir at 82° C. for 1 h and then stirred overnight at room temperature. The mixture was then filtered, and the solid rinsed with IPA, and dried in vacuo at 60° C. for 3 days to yield sodium 4-{4-[4-(3-methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylate (96.9%).

Workup

  1. stirringstirred overnight at room temperature
  2. filtrationThe mixture was then filtered
  3. washthe solid rinsed with IPA
  4. customdried in vacuo at 60° C. for 3 days

Sources & evidence

ORD record
ord-b35a96e046774f5597471ec4b2a42eb0
Source dataset
uspto-grants-2014_02
Patent number
US08642601B2

Linked notes

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