Hydrochloric Acid → HCID 9979653, compound

HRID 969670Notes

Reaction equation

HRID 969670 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH:13][C:14](=[O:33])[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[NH:21][CH2:22][C:23]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:26]=[CH:25][CH:24]=3)[CH:11]=2)[C:6]([CH3:35])([CH3:34])[CH2:5]1)(=O)C.Cl>CCO>[CH3:34][C:6]1([CH3:35])[C:7]2[C:12](=[CH:11][C:10]([NH:13][C:14](=[O:33])[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[NH:21][CH2:22][C:23]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:26]=[CH:25][CH:24]=3)=[CH:9][CH:8]=2)[NH:4][CH2:5]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 9981906HCID 9981906, compound

Product 1

HCID 9979653HCID 9979653, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-(1-Acetyl-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-2-[(quinolin-4-ylmethyl)-amino]-benzamide (Example 9) (150 mg, 0.32 mmol) was dissolved in EtOH (15 mL) and concentrated aqueous HCl (5 mL) and the mixture was heated to 50° C. overnight, then 80° C. for 2 h. After drying in vacuo, the residue was partitioned between CH2Cl2 and aqueous NaHCO3. The organic layer was collected, washed with brine, and dried over Na2SO4. After concentrated in vacuo, the desired product was isolated as a white solid. MS: (ES+) 423, (M+H). Calc'd. for C27H26N4O-422.53.

Workup

  1. customAfter drying in vacuo
  2. customthe residue was partitioned between CH2Cl2 and aqueous NaHCO3
  3. customThe organic layer was collected
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationAfter concentrated in vacuo

Sources & evidence

ORD record
ord-c5dbc1fab2fc44498bd1ddb13f5b1be3
Source dataset
uspto-grants-2007_12
Patent number
US07307088B2

Reaction notes

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