Sodium Chloride → HCID 178486469, compound

HRID 1014464Notes

Reaction equation

HRID 1014464 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:44][CH3:45])=[C:10]([NH:13][C:14]3[N:15]=[C:16]([NH:33][C:34]4[CH:42]=[CH:41][CH:40]=[C:39]([F:43])[C:35]=4[C:36]([NH2:38])=[O:37])[C:17]4[CH:22]=[CH:21][N:20](S(C5C=CC(C)=CC=5)(=O)=O)[C:18]=4[N:19]=3)[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C[O-].[Na+].[Na+].[Cl-]>CO.C1COCC1.CCOC(C)=O>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:44][CH3:45])=[C:10]([NH:13][C:14]3[NH:19][C:18]4=[N:20][CH:21]=[CH:22][C:17]4=[C:16]([NH:33][C:34]4[CH:42]=[CH:41][CH:40]=[C:39]([F:43])[C:35]=4[C:36]([NH2:38])=[O:37])[N:15]=3)[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 5234Sodium ChlorideHCID 10942334Sodium MethoxideHCID 59441879HCID 59441879, compound

Product 1

HCID 178486469HCID 178486469, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of of 2-({2-{[1-acetyl-5-(methyloxy)-2,3-dihydro-1H-indol-6-yl]amino}-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-6-fluorobenzamide (104 mg, 0.17 mmol) in methanol (10 mL) and THF (20 mL) was treated with a solution of sodium methoxide (0.5M in MeOH, 3.3 mL, 1.7 mmol). The resulting mixture was stirred at rt for 2 days, then diluted with EtOAc (100 mL) and a saturated NaCl solution. The organic layer was washed with a saturated NaHCO3 solution, concentrated onto Celite and purified by silica gel chromatography using 0-5% MeOH (containing 0.2% NH3)/CH2Cl2 to obtain 2-[(2-{[1-acetyl-5-(methyloxy)-2,3-dihydro-1H-indol-6-yl]amino}-1H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-6-fluorobenzamide as a yellow solid (63 mg, 81%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.13 (s, 3H), 3.09-3.19 (m, 2H), 3.78 (s, 3H), 4.06-4.15 (m, 2H), 6.23 (s, 1H), 6.88 (J=9.71 Hz, 9.34 Hz, 1H), 6.95 (s, 2H), 7.27-7.37 (m, 1H), 7.58 (s, 1H), 8.02 (s, 1H), 8.10 (s, 1H), 8.50 (d, J=8.42 Hz, 1H), 8.62 (s, 1H), 10.52 (s, 1H), 11.29 (s, 1H); ESIMS (M+H)+=475.99.

Workup

  1. washThe organic layer was washed with a saturated NaHCO3 solution
  2. concentrationconcentrated onto Celite
  3. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-390a0689dacc4f5cae4faaf397c60623
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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