Water → HCID 178485535, compound

HRID 1014561Notes

Reaction equation

HRID 1014561 reaction equation
[CH3:1][N:2]([CH3:50])[CH2:3][C:4]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:48][CH3:49])=[C:12]([NH:15][C:16]3[N:17]=[C:18]([NH:36][C:37]4[CH:46]=[CH:45][CH:44]=[C:43]([F:47])[C:38]=4[C:39]([NH:41][CH3:42])=[O:40])[C:19]4[C:24]([CH3:25])=[CH:23][N:22](S(C5C=CC(C)=CC=5)(=O)=O)[C:20]=4[N:21]=3)[CH:13]=2)[CH2:8][CH2:7]1)=[O:5].[OH-].[Na+].O>O1CCOCC1.CCOC(C)=O>[CH3:50][N:2]([CH3:1])[CH2:3][C:4]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:48][CH3:49])=[C:12]([NH:15][C:16]3[NH:21][C:20]4=[N:22][CH:23]=[C:24]([CH3:25])[C:19]4=[C:18]([NH:36][C:37]4[CH:46]=[CH:45][CH:44]=[C:43]([F:47])[C:38]=4[C:39]([NH:41][CH3:42])=[O:40])[N:17]=3)[CH:13]=2)[CH2:8][CH2:7]1)=[O:5]

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 67316596HCID 67316596, compound

Product 1

HCID 178485535HCID 178485535, compoundYield 70.7%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

2-({2-{[1-(N,N-dimethylglycyl)-5-(methyloxy)-2,3-dihydro-1H-indol-6-yl]amino}-5-methyl-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-6-fluoro-N-methylbenzamide (225 mg, 0.321 mmol) was dissolved in dioxane (6 mL), 6N NaOH (2 mL) and water (2 mL) was added in a microwave safe vessel. The reaction was then heated in a microwave at 120° C. for 23 min. Reaction was diluted with EtOAc and the organic layer was washed with water and a saturated brine solution and dried over sodium sulfate. Solvents were removed under reduced pressure and the residue purified by chromatography on SiO2 to afford 2-[(2-{[1-(N,N-dimethylglycyl)-5-(methyloxy)-2,3-dihydro-1H-indol-6-yl]amino}-5-methyl-1H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-6-fluoro-N-methylbenzamide (124 mg, 0.227 mmol) as an off white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.25 (s, 6 H) 2.41 (s, 3 H) 2.81 (d, J=4.39 Hz, 3 H) 3.12 (t, J=8.24 Hz, 2 H) 3.17 (s, 2 H) 3.76 (s, 3 H) 4.18 (t, J=8.33 Hz, 2 H) 6.68 (s, 1 H) 6.86 (t, J=9.25 Hz, 1 H) 6.95 (s, 1 H) 7.25 (d, J=7.14 Hz, 1 H) 7.52 (s, 1 H) 8.45 (d, J=8.42 Hz, 1 H) 8.57 (s, 1 H) 8.66 (d, J=4.39 Hz, 1 H) 9.44 (s, 1 H) 10.92 (s, 1 H). ESIMS (M+H)+=547.

Workup

  1. customReaction
  2. washthe organic layer was washed with water
  3. dry with materiala saturated brine solution and dried over sodium sulfate
  4. customSolvents were removed under reduced pressure
  5. customthe residue purified by chromatography on SiO2

Sources & evidence

ORD record
ord-1eee09363f954d0cabb7da7a8e699a1e
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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