Sodium Hydroxide → HCID 57731644, compound

HRID 2234655Notes

Reaction equation

HRID 2234655 reaction equation
[CH:1]1([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([C:19]4[CH:24]=[CH:23][C:22]([NH:25][C:26]([N:28]5[CH2:33][CH2:32][O:31][CH2:30][CH2:29]5)=[O:27])=[C:21]([C:34](=[O:38])[N:35]([CH3:37])[CH3:36])[CH:20]=4)[CH:17]=3)[N:12](COC(=O)C(C)(C)C)[CH:11]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][O:2]1.[OH-].[Na+]>O1CCCC1.CO>[CH:1]1([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([C:19]4[CH:24]=[CH:23][C:22]([NH:25][C:26]([N:28]5[CH2:29][CH2:30][O:31][CH2:32][CH2:33]5)=[O:27])=[C:21]([C:34](=[O:38])[N:35]([CH3:36])[CH3:37])[CH:20]=4)[CH:17]=3)[NH:12][CH:11]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][O:2]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68694197HCID 68694197, compound

Product 1

HCID 57731644HCID 57731644, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2,2-dimethyl-propionic acid 3-(1,3-dihydro-isobenzofuran-1-yl)-5-{3-dimethylcarbamoyl-4-[(morpholine-4-carbonyl)-amino]-phenyl}-pyrrolo[2,3-b]pyridin-1-ylmethyl ester was dissolved in tetrahydrofuran. 1 M sodium hydroxide in methanol was added to the mixture, and the reaction was stirred for 2 hours at room temperature. The reaction was quenched with sodium bicarbonate solution and extracted with dichloromethane. The organic layer was dried, filtered, and concentrated. The crude material was purified then by mass-triggered reverse-phase HPLC to afford morpholine-4-carboxylic acid {4-[3-(1,3-dihydro-isobenzofuran-1-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-dimethylcarbamoyl-phenyl}-amide. 1H NMR (250 MHz, DMSO-d6) δ 11.74 (s, 1H), 8.75 (s, 1H), 8.47 (s, 1H), 7.69 (d, J=8.7 Hz, 1H), 7.55-7.49 (m, 3H), 7.44-7.22 (m, 4H), 7.10 (d, J=7.6 Hz, 1H), 6.48 (s, 1H), 5.13 (m, 2H), 3.62-3.58 (m, 4H), 3.42-3.35 (m, 4H in water peak), 2.98 (s, 3H), 2.94 (s, 3H); MS: m/z 512.3 (M+H+).

Workup

  1. customThe reaction was quenched with sodium bicarbonate solution
  2. extractionextracted with dichloromethane
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified

Sources & evidence

ORD record
ord-428a8f0774994009ad09ba82f5a8cae6
Source dataset
uspto-grants-2010_05
Patent number
US07709645B2

Reaction notes

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