Ethyl Acetate → HCID 178485541, compound

HRID 1014538Notes

Reaction equation

HRID 1014538 reaction equation
[CH3:1][N:2]([CH3:47])[CH2:3][C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([O:45][CH3:46])=[C:11]([NH:13][C:14]2[N:15]=[C:16]([NH:33][C:34]3[CH:43]=[CH:42][CH:41]=[C:40]([F:44])[C:35]=3[C:36]([NH:38][CH3:39])=[O:37])[C:17]3[CH:22]=[CH:21][N:20](S(C4C=CC(C)=CC=4)(=O)=O)[C:18]=3[N:19]=2)[CH:12]=1)=[O:5].[OH-].[K+].CCOC(C)=O.C([O-])(O)=O.[Na+]>O1CCOCC1>[CH3:47][N:2]([CH3:1])[CH2:3][C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([O:45][CH3:46])=[C:11]([NH:13][C:14]2[NH:19][C:18]3=[N:20][CH:21]=[CH:22][C:17]3=[C:16]([NH:33][C:34]3[CH:43]=[CH:42][CH:41]=[C:40]([F:44])[C:35]=3[C:36]([NH:38][CH3:39])=[O:37])[N:15]=2)[CH:12]=1)=[O:5]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 516892Sodium BicarbonateHCID 59441920HCID 59441920, compound

Product 1

HCID 178485541HCID 178485541, compoundYield 59.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-({2-{[5-[(N,N-dimethylglycyl)amino]-2-(methyloxy)phenyl]amino}-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-6-fluoro-N-methylbenzamide (485 mg, 0.734 mmol) and a 1M aqueous KOH solution (7.34 mL, 7.34 mmol) in dioxane (20 mL) was heated at 80° C. for 7 h. The resulting mixture was allowed to cool to rt. EtOAc (50 mL) was added, followed by a saturated NaHCO3 solution (50 mL). The organic layer was washed with a saturated NaCl solution (50 mL), concentrated onto Celite and purified by silica gel chromatography using 1-10% MeOH (containing 0.2% NH3)/CH2Cl2 to obtain 2-[(2-{[5-[(N,N-dimethylglycyl)amino]-2-(methyloxy)phenyl]amino}-1H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-6-fluoro-N-methylbenzamide as a white solid (220 mg, 59%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.28 (s, 6H), 2.80 (d, J=4.58 Hz, 3H), 3.03 (s, 2H), 3.82 (s, 3H), 6.31 (dd, J=3.48, 1.83 Hz, 1H), 6.89-7.03 (m, 3H), 7.33 (dd, J=8.79, 2.56 Hz, 1H), 7.36-7.45 (m, 1H), 7.57 (s, 1H), 8.21 (d, J=2.38 Hz, 1H), 8.31 (d, J=8.24 Hz, 1H), 8.51-8.61 (m, 1H), 9.40 (s, 1H), 10.17 (s, 1H), 11.35 (s, 1H); ESIMS (M+H)+=507.

Workup

  1. washThe organic layer was washed with a saturated NaCl solution (50 mL)
  2. concentrationconcentrated onto Celite
  3. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-373bc0d020654c3fa8f5489d56184272
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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