Ethyl Acetate → HCID 178492392, compound

HRID 1014536Notes

Reaction equation

HRID 1014536 reaction equation
[CH3:1][N:2]([CH3:46])[CH2:3][C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([O:44][CH3:45])=[C:11]([NH:13][C:14]2[N:15]=[C:16]([NH:33][C:34]3[CH:42]=[CH:41][CH:40]=[C:39]([F:43])[C:35]=3[C:36]([NH2:38])=[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>[CH3:1][N:2]([CH3:46])[CH2:3][C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([O:44][CH3:45])=[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:42]=[CH:41][CH:40]=[C:39]([F:43])[C:35]=3[C:36]([NH2:38])=[O:37])[N:15]=2)[CH:12]=1)=[O:5]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 516892Sodium BicarbonateHCID 59441932HCID 59441932, compound

Product 1

HCID 178492392HCID 178492392, compoundYield 48%

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-fluorobenzamide (362 mg, 0.560 mmol) and a 1M aqueous KOH solution (5.60 mL, 5.60 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-fluorobenzamide as a yellow solid (131 mg, 48%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.28 (s, 6H), 3.03 (s, 2H), 3.82 (s, 3H), 6.26 (dd, J=3.30, 1.83 Hz, 1H), 6.87-6.98 (m, 2H), 7.01 (dd, J=3.39, 2.29 Hz, 1H), 7.34 (dd, J=8.79, 2.56 Hz, 1H), 7.36-7.46 (m, 1H), 7.60 (s, 1H), 8.04 (s, 1H), 8.11 (s, 1H), 8.20 (d, J=2.56 Hz, 1H), 8.47 (d, J=8.42 Hz, 1H), 9.41 (s, 1H), 10.55 (s, 1H), 11.37 (s, 1H); ESIMS (M+H)+=493.

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-ae2024a7e97049b0b2eadeaddcc94ffb
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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