Sodium Hydroxide → HCID 178485525, compound

HRID 1014562Notes

Reaction equation

HRID 1014562 reaction equation
[CH3:1][N:2]([CH3:51])[CH2:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([O:49][CH3:50])=[C:13]([NH:16][C:17]3[N:18]=[C:19]([NH:37][C:38]4[CH:47]=[CH:46][CH:45]=[C:44]([F:48])[C:39]=4[C:40]([NH:42][CH3:43])=[O:41])[C:20]4[C:25]([CH3:26])=[CH:24][N:23](S(C5C=CC(C)=CC=5)(=O)=O)[C:21]=4[N:22]=3)[CH:14]=2)[CH2:9][CH2:8][CH2:7]1)=[O:5].[OH-].[Na+]>O1CCOCC1.CCOC(C)=O>[CH3:51][N:2]([CH3:1])[CH2:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([O:49][CH3:50])=[C:13]([NH:16][C:17]3[NH:22][C:21]4=[N:23][CH:24]=[C:25]([CH3:26])[C:20]4=[C:19]([NH:37][C:38]4[CH:47]=[CH:46][CH:45]=[C:44]([F:48])[C:39]=4[C:40]([NH:42][CH3:43])=[O:41])[N:18]=3)[CH:14]=2)[CH2:9][CH2:8][CH2:7]1)=[O:5]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67317193HCID 67317193, compound

Product 1

HCID 178485525HCID 178485525, compoundYield 67.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

2-({2-{[1-(N,N-dimethylglycyl)-6-(methyloxy)-1,2,3,4-tetrahydro-7-quinolinyl]amino}-5-methyl-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-6-fluoro-N-methylbenzamide (249 mg, 0.348 mmol) was dissolved in dioxane (3 mL) and 2N NaOH (2 mL) was added in a microwave safe vessel. The reaction was then heated in a microwave at 120° C. for 17 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)-6-(methyloxy)-1,2,3,4-tetrahydro-7-quinolinyl]amino}-5-methyl-1H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-6-fluoro-N-methylbenzamide (132 mg, 0.235 mmol) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.83-1.93 (m, 2 H) 2.11 (br. s., 6 H) 2.42 (s, 3H) 2.68 (br. s., 2 H) 2.81 (d, J=4.49 Hz, 3 H) 3.21 (s, 2 H) 3.66-3.74 (m, 2 H) 3.84 (s, 3 H) 6.70-6.78 (m, 1 H) 6.79-6.88 (m, 1 H) 6.88-6.98 (m, 1 H) 7.31-7.41 (m, 1H) 7.43 (s, 1 H) 8.34-8.42 (m, 2 H) 8.63-8.72 (m, 1 H) 9.49-9.59 (m, 1 H) 11.00-11.12 (m, 1 H). ESIMS (M+H)+=561

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-af5da4bf5c48406fa8c06b6692d74a49
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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