Dichloromethane → HCID 59447972, compound

HRID 1916295Notes

Reaction equation

HRID 1916295 reaction equation
C[O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]3[C:17]([N:18]4[CH2:23][CH2:22][O:21][CH:20]([CH2:24][NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:19]4)=[N:16][CH:15]=[N:14][C:10]=3[NH:11]2)=[CH:7][CH:6]=1)=[O:4].[OH-].[Na+].C(Cl)Cl>CO>[C:29]([O:28][C:26]([NH:25][CH2:24][CH:20]1[O:21][CH2:22][CH2:23][N:18]([C:17]2[C:9]3[C:8]4[C:12](=[CH:13][C:5]([C:3]([OH:4])=[O:2])=[CH:6][CH:7]=4)[NH:11][C:10]=3[N:14]=[CH:15][N:16]=2)[CH2:19]1)=[O:27])([CH3:32])([CH3:30])[CH3:31]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 68517179HCID 68517179, compound

Product 1

HCID 59447972HCID 59447972, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 4-[2-(tert-Butoxycarbonylamino-methyl)-morpholin-4-yl]9H-pyrimido[4,5-b]indole-7-carboxylic acid methyl ester (35 mg, 0.079 mmol) in methanol (2 mL) was treated with NaOH (1 mL, 4 M in dioxane, 4 mmol) and left overnight at room temperature. DCM (5 mL) was added to the reaction mixture. The aqueous layer was collected and acidified with 1M HCl, evaporated to dryness and suspended in water. The resulting precipitate was collected by filtration as a white solid (12 mg, 0.028 mmol). LC-MS (1) Rt 1.17 min; m/z (ES−) 426.

Workup

  1. customThe aqueous layer was collected
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-ae61e1dfe25c414daa2c19b221dfa58c
Source dataset
uspto-grants-2013_12
Patent number
US08618121B2

Reaction notes

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