Ethyl Acetate → HCID 178421856, compound

HRID 1014540Notes

Reaction equation

HRID 1014540 reaction equation
[CH3:1][N:2]([CH3:48])[CH2:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([CH3:47])=[C:13]([NH:16][C:17]3[N:18]=[C:19]([NH:36][C:37]4[CH:45]=[CH:44][CH:43]=[C:42]([F:46])[C:38]=4[C:39]([NH2:41])=[O:40])[C:20]4[CH:25]=[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-].[K+].CCOC(C)=O.C([O-])(O)=O.[Na+]>O1CCOCC1>[CH3:1][N:2]([CH3:48])[CH2:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([CH3:47])=[C:13]([NH:16][C:17]3[NH:22][C:21]4=[N:23][CH:24]=[CH:25][C:20]4=[C:19]([NH:36][C:37]4[CH:45]=[CH:44][CH:43]=[C:42]([F:46])[C:38]=4[C:39]([NH2:41])=[O:40])[N:18]=3)[CH:14]=2)[CH2:9][CH2:8][CH2:7]1)=[O:5]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 516892Sodium BicarbonateHCID 59441705HCID 59441705, compound

Product 1

HCID 178421856HCID 178421856, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-({2-{[1-(N,N-dimethylglycyl)-6-methyl-1,2,3,4-tetrahydro-7-quinolinyl]amino}-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-6-fluorobenzamide (414 mg, 0.617 mmol) and a 1N aqueous KOH solution (6.17 mL, 6.17 mmol) in dioxane (20 mL) was heated at 80° C. for 17 h. EtOAc (50 mL) and a saturated NaHCO3 solution (50 mL) were added. 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 afford 2-[(2-{[1-(N,N-dimethylglycyl)-6-methyl-1,2,3,4-tetrahydro-7-quinolinyl]amino}-1H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-6-fluorobenzamide as a white solid (237 mg, 74%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.82-1.96 (m, 2H), 2.12 (s, 6H), 2.17 (s, 3H), 2.70 (t, J=6.50 Hz, 2H), 3.17 (s, 2H), 3.72 (t, J=6.04 Hz, 2H), 6.19 (dd, H=3.39, 1.92 Hz, 1H), 6.82-6.91 (m, 1H), 6.93 (dd, J=3.39, 2.29 Hz, 1H), 7.00 (s, 1H), 7.19-7.30 (m, 1H), 7.78 (br s, 1H), 8.00 (s, 1H), 8.09 (s, 1H), 8.11 (s, 1H), 8.47 (d, J=8.61 Hz, 1H), 10.54 (s, 1H), 11.24 (s, 1H); ESIMS (M+H)+=517.26.

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-c782ab67676b4e67b2558c434b264b22
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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