Sodium Hydroxide → HCID 178486467, compound

HRID 1014563Notes

Reaction equation

HRID 1014563 reaction equation
[CH3:1][N:2]([CH3:50])[CH2:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([O:48][CH3:49])=[C:13]([NH:16][C:17]3[N:18]=[C:19]([NH:37][C:38]4[CH:46]=[CH:45][CH:44]=[C:43]([F:47])[C:39]=4[C:40]([NH2:42])=[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>[CH3:50][N:2]([CH3:1])[CH2:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([O:48][CH3:49])=[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:46]=[CH:45][CH:44]=[C:43]([F:47])[C:39]=4[C:40]([NH2:42])=[O:41])[N:18]=3)[CH:14]=2)[CH2:9][CH2:8][CH2:7]1)=[O:5]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67316766HCID 67316766, compound

Product 1

HCID 178486467HCID 178486467, compoundYield 78.4%

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-fluorobenzamide (146 mg, 0.208 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 10 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-fluorobenzamide (89 mg, 0.163 mmol) as a pink solid. 1 H NMR (400 MHz, DMSO-d6) δ ppm 1.81-1.92 (m, 2 H) 2.10 (br. s., 6 H) 2.42 (s, 3 H) 2.67 (br. s., 2 H) 3.20 (s, 2 H) 3.66-3.74 (m, 2 H) 3.84 (s, 3 H) 6.74 (s, 1 H) 6.79-6.86 (m, 1 H) 6.86-6.96 (m, 1 H) 7.31-7.40 (m, 1 H) 7.42 (s, 1 H) 8.12 (d, J=14.92 Hz, 2 H) 8.40 (d, J=8.61 Hz, 2 H) 9.88 (s, 1 H) 10.99-11.11 (m, 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-cda49a83dbc74579ab7e9ae9ade81ea9
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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