Sodium Hydroxide → HCID 49820978, compound

HRID 1692871Notes

Reaction equation

HRID 1692871 reaction equation
[CH3:1][N:2]1[C:10]([CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[CH2:14][CH2:13]2)=[N:9][C:8]2[C:3]1=[N:4][C:5]([C:30]1[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[N:32](S(C3C=CC=CC=3)(=O)=O)[CH:31]=1)=[N:6][C:7]=2[N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.[OH-].[Na+]>C(O)C>[NH:32]1[C:33]2[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:30]([C:5]2[N:4]=[C:3]3[C:8]([N:9]=[C:10]([CH2:11][N:12]4[CH2:13][CH2:14][CH:15]([N:18]5[CH2:23][CH2:22][O:21][CH2:20][CH2:19]5)[CH2:16][CH2:17]4)[N:2]3[CH3:1])=[C:7]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[N:6]=2)=[CH:31]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 596035014-(1-((9-methyl-6-morpholino-2-(1-(phenylsulfonyl)-1H-indol-3-yl)-9H-purin-8-yl)methyl)piperidin-4-yl)morpholine

Product 1

HCID 49820978HCID 49820978, compoundYield 57.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-(1-((9-methyl-6-morpholino-2-(1-(phenylsulfonyl)-1H-indol-3-yl)-9H-purin-8-yl)methyl)piperidin-4-yl)morpholine (357 mg, 0.544 mmol) in ethanol (5 mL) was added a 1 M aqueous solution of NaOH (4 mL, 4 mmol). After 18 hours of stirring, the reaction mixture was concentrated and purified by RP-HPLC to give 104 (162 mg, 57.7%). LCMS: M+H+=517.3. 1H-NMR (400 MHz, DMSO-d6): δ 11.46 (s, 1H), 8.60 (m, 1H), 8.13 (s, 1H), 7.43 (m, 1H), 7.14 (m, 2H), 4.16 (s, 4H), 3.84, (s, 3H), 3.76 (t, 4H), 3.71 (s, 2H), 3.54 (t, 4H), 2.85 (d, 2H), 2.43 (t, 4H), 2.07 (m, 3H), 1.75 (d, 2H), 1.38 (m, 2H)

Workup

  1. concentrationthe reaction mixture was concentrated
  2. custompurified by RP-HPLC

Sources & evidence

ORD record
ord-0c1ed380ff8b4e88b8838af5106340da
Source dataset
uspto-grants-2012_04
Patent number
US08158625B2

Reaction notes

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