Hydrochloric Acid → HCID 69267338, compound

HRID 2196587Notes

Reaction equation

HRID 2196587 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH:13][C:14]([C:16]3[C:17]4[CH2:18][CH2:19][N:20]([CH2:26][C:27]5[C:36]6[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=6)[N:30]=[CH:29][CH:28]=5)[CH2:21][C:22]=4[CH:23]=[CH:24][CH:25]=3)=[O:15])[CH:11]=2)[C:6]([CH3:38])([CH3:37])[CH2:5]1)(=O)C.Cl>C(O)C>[CH3:37][C:6]1([CH3:38])[C:7]2[C:12](=[CH:11][C:10]([NH:13][C:14]([C:16]3[C:17]4[CH2:18][CH2:19][N:20]([CH2:26][C:27]5[C:36]6[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=6)[N:30]=[CH:29][CH:28]=5)[CH2:21][C:22]=4[CH:23]=[CH:24][CH:25]=3)=[O:15])=[CH:9][CH:8]=2)[NH:4][CH2:5]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59756872HCID 59756872, compound

Product 1

HCID 69267338HCID 69267338, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

N-(1-Acetyl-3,3-dimethylindolin-6-yl)-2-(quinolin-4-ylmethyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxamide (55 mg, 0.109 mmol) was mostly dissolved in ethanol (1.25 mL) then added concentrated hydrochloric acid (0.745 mL). The reaction mixture was heated at 60° C. for 6 hours. The mixture was concentrated under vacuum and the remaining residue diluted with a small amount of water. The solution was brought to pH 9-10 with the addition of 6N aqueous sodium hydroxide. A precipitate formed which was collected on a glass frit, washing with minimal water then dichloromethane. The solid was dried under high vacuum to afford 35 mg of N-(3,3-dimethylindolin-6-yl)-2-(quinolin-4-ylmethyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxamide as a tan solid. MS (ESI, pos. ion) m/z: 463.2 (M+1)

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. additionthe remaining residue diluted with a small amount of water
  3. additionThe solution was brought to pH 9-10 with the addition of 6N aqueous sodium hydroxide
  4. customA precipitate formed which
  5. customwas collected on a glass frit
  6. washwashing with minimal water
  7. customThe solid was dried under high vacuum

Sources & evidence

ORD record
ord-6cbbc91b8aea4123897e5dac00b83600
Source dataset
uspto-grants-2012_12
Patent number
US08338455B2

Reaction notes

Loading…