HCID 11641773, compound → HCID 58588142, compound

HRID 1361691Notes

Reaction equation

HRID 1361691 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH:13][C:14](=[O:35])[C:15]3[CH:20]=[CH:19][C:18]([F:21])=[C:17]([NH:22][C:23]4[C:28]([C:29]5[CH:34]=[CH:33][N:32]=[CH:31][N:30]=5)=[CH:27][CH:26]=[CH:25][N:24]=4)[CH:16]=3)[CH:11]=2)[C:6]([CH3:37])([CH3:36])[CH2:5]1)(=O)C>C(O)C>[CH3:36][C:6]1([CH3:37])[C:7]2[C:12](=[CH:11][C:10]([NH:13][C:14](=[O:35])[C:15]3[CH:20]=[CH:19][C:18]([F:21])=[C:17]([NH:22][C:23]4[C:28]([C:29]5[CH:34]=[CH:33][N:32]=[CH:31][N:30]=5)=[CH:27][CH:26]=[CH:25][N:24]=4)[CH:16]=3)=[CH:9][CH:8]=2)[NH:4][CH2:5]1

Participants

3

Reactant 1

HCID 11641773HCID 11641773, compound

Product 1

HCID 58588142HCID 58588142, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
47 °C

Procedure

N-(1-Acetyl-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-4-fluoro-3-(3-pyrimidin-4-yl-pyridin-2-ylamino)-benzamide (137 mg, 0.28 mmol, Example Norman) was dissolved in 3:1 ethanol/concentrated HCl and heated under N2 at 47° C. for 20 h. After concentration, the residue was diluted with sat'd aqueous NaHCO3 and extracted with EtOAc. The organic layer was dried with Na2SO4, concentrated, triturated with methanol, and filtered to provide yellow solid product. MS m/z=455 [M+H]+. Calc'd for C26H23FN6O: 454.51.

Workup

  1. concentrationAfter concentration
  2. additionthe residue was diluted with sat'd aqueous NaHCO3
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried with Na2SO4
  5. concentrationconcentrated
  6. customtriturated with methanol
  7. filtrationfiltered
  8. customto provide yellow solid product

Sources & evidence

ORD record
ord-db71a0795fa2430f890937411d61a7c4
Source dataset
uspto-grants-2011_02
Patent number
US07880000B2

Reaction notes

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