Hydrogen chloride-ethyl acetate → 1-{[(4aR*,6R*,8aR*)-3-Cyano-8-methyl-2-(methylamino)-4H,4aH,5H,6H,7H,8H,8aH,9H-thieno[3,2-g]quinolin-6-yl]carbonyl}-3-[3-(dimethylamino)propyl]-1-propylurea di hydrochloride salt

HRID 2280216Notes

Reaction equation

HRID 2280216 reaction equation
[C:1]([C:3]1[C:7]2[CH2:8][C@@H:9]3[C@@H:14]([CH2:15][C:6]=2[S:5][C:4]=1[N:32](C)[C:33](=O)OC(C)(C)C)[N:13]([CH3:16])[CH2:12][C@H:11]([C:17]([N:19]([C:23](=[O:31])[NH:24][CH2:25][CH2:26][CH2:27][N:28]([CH3:30])[CH3:29])[CH2:20][CH2:21][CH3:22])=[O:18])[CH2:10]3)#[N:2].C(OCC)(=O)C.[ClH:47]>C(OCC)(=O)C>[ClH:47].[ClH:47].[C:1]([C:3]1[C:7]2[CH2:8][C@@H:9]3[C@@H:14]([CH2:15][C:6]=2[S:5][C:4]=1[NH:32][CH3:33])[N:13]([CH3:16])[CH2:12][C@H:11]([C:17]([N:19]([CH2:20][CH2:21][CH3:22])[C:23]([NH:24][CH2:25][CH2:26][CH2:27][N:28]([CH3:30])[CH3:29])=[O:31])=[O:18])[CH2:10]3)#[N:2]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetate2×HCID 86731032tert-butyl N-[(4aR*,6R*,8aR*)-3-cyano-6-[({[3-(dimethylamino)propyl]carbamoyl}(propyl)amino)carbonyl]-8-methyl-4H,4aH,5H,6H,7H,8H,8a H,9H-thieno[3,2-g]quinolin-2-yl]-N-methylcarbamate

Product 1

HCID 867310331-{[(4aR*,6R*,8aR*)-3-Cyano-8-methyl-2-(methylamino)-4H,4aH,5H,6H,7H,8H,8aH,9H-thieno[3,2-g]quinolin-6-yl]carbonyl}-3-[3-(dimethylamino)propyl]-1-propylurea di hydrochloride salt

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of tert-butyl N-[(4aR*,6R*,8aR*)-3-cyano-6-[({[3-(dimethylamino)propyl]carbamoyl}(propyl)amino)carbonyl]-8-methyl-4H,4aH,5H,6H,7H,8H,8a H,9H-thieno[3,2-g]quinolin-2-yl]-N-methylcarbamate (118 mg) and ethyl acetate (10 mL) was added a 4 mol/L hydrogen chloride-ethyl acetate solution (5 mL) while stirring at room temperature, and the mixture was stirred at the same temperature for 11 hours. To the reaction mixture were added a 4 mol/L hydrogen chloride-ethyl acetate solution (5 mL) while stirring at room temperature, and then stirred at the same temperature for 14 hours. The solid was collected by filtration to give the title compound (compound 3-2) (45 mg). The structure was illustrated in Table 11.

Workup

  1. stirringthe mixture was stirred at the same temperature for 11 hours
  2. stirringwhile stirring at room temperature
  3. stirringstirred at the same temperature for 14 hours
  4. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-69e1b426a2b340f698bc00c9944fada0
Source dataset
uspto-grants-2015_09
Patent number
US09138434B2

Reaction notes

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