Sodium Hydroxide → HCID 178493018, compound

HRID 1014436Notes

Reaction equation

HRID 1014436 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]([NH:12][C:13]2[C:14]3[CH:39]=[CH:38][N:37](S(C4C=CC(C)=CC=4)(=O)=O)[C:15]=3[N:16]=[C:17]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([N:26]4[CH2:31][CH2:30][N:29]([CH:32]([CH3:34])[CH3:33])[CH2:28][CH2:27]4)=[CH:22][C:21]=3[O:35][CH3:36])[N:18]=2)[C:3]=1[C:4]([NH2:6])=[O:5].[OH-].[Na+]>O1CCOCC1.C(OCC)(=O)C>[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]([NH:12][C:13]2[N:18]=[C:17]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([N:26]4[CH2:27][CH2:28][N:29]([CH:32]([CH3:33])[CH3:34])[CH2:30][CH2:31]4)=[CH:22][C:21]=3[O:35][CH3:36])[NH:16][C:15]3=[N:37][CH:38]=[CH:39][C:14]=23)[C:3]=1[C:4]([NH2:6])=[O:5]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 673173812,4-difluoro-6-({2-{[4-[4-(1-methylethyl)-1-piperazinyl]-2-(methyloxy)phenyl]amino}-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)benzamide

Product 1

HCID 178493018HCID 178493018, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

2,4-difluoro-6-({2-{[4-[4-(1-methylethyl)-1-piperazinyl]-2-(methyloxy)phenyl]amino}-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)benzamide (175 mg, 0.254 mmol) was suspended in a mixture of dioxane (10 mL) and aqueous 2.0N NaOH (5 mL) and stirred rapidly under microwave heating (120° C.) for 10 minutes. After cooling, the reaction mixture was diluted with ethyl acetate and washed with saturated sodium chloride. The organic layer was dried over sodium sulfate, taken to a residue under reduced pressure, and purified by chromatography on SiO2 to afford 2,4-difluoro-6-[(2-{[4-[4-(1-methylethyl)-1-piperazinyl]-2-(methyloxy)phenyl]amino}-1H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]benzamide as a pale yellow solid (85 mg, 63% yield); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.00 (d, J=6.60 Hz, 6H), 2.52-2.61 (m, 4H), 2.66 (d, J=6.23 Hz, 1H), 3.08 (d, J=5.50 Hz, 4H), 3.78 (s, 3H), 6.18 (dd, J=3.67, 1.83 Hz, 1H), 6.45 (dd, J=8.80, 2.57 Hz, 1H), 6.61 (d, J=2.57 Hz, 1H), 6.89 (ddd, J=11.36, 8.80, 2.57 Hz, 1H), 6.93-6.98 (m, 1H), 7.59 (s, 1H), 7.68 (d, J=8.80 Hz, 1H), 8.01 (d, J=1.47 Hz, 1H), 8.15 (s, 1H), 8.56 (d, J=11.73 Hz, 1H), 11.08 (s, 1H), 11.32 (s, 1H). ESIMS (M+H)+=537.

Workup

  1. temperatureAfter cooling
  2. washwashed with saturated sodium chloride
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. custompurified by chromatography on SiO2

Sources & evidence

ORD record
ord-1f048b37a83b431f8070de1afb737457
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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