Dichloromethane → HCID 59447972, compound

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

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.