Hydrochloric Acid → HCID 86731035, compound

HRID 2280217Notes

Reaction equation

HRID 2280217 reaction equation
[NH2:1][C:2]1[S:14][C:13]2[CH2:12][C@@H:11]3[C@H:6]([CH2:7][C@@H:8]([C:16]([N:18]([CH2:27][CH2:28][CH3:29])[C:19]([NH:21][CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])=[O:20])=[O:17])[CH2:9][N:10]3[CH3:15])[CH2:5][C:4]=2[C:3]=1[C:30]#[N:31].[ClH:32]>C(O)C>[ClH:32].[ClH:32].[NH2:1][C:2]1[S:14][C:13]2[CH2:12][C@@H:11]3[C@H:6]([CH2:7][C@@H:8]([C:16]([N:18]([CH2:27][CH2:28][CH3:29])[C:19]([NH:21][CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])=[O:20])=[O:17])[CH2:9][N:10]3[CH3:15])[CH2:5][C:4]=2[C:3]=1[C:30]#[N:31]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 665485291399442-97-72×

Product 1

HCID 86731035HCID 86731035, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a mixture of 1-{[(4aR,6R,8aR)-2-amino-3-cyano-8-methyl-4H,4aH,5H, 6H,7H,8H,8aH,9H-thieno[3,2-g]quinolin-6-yl]carbonyl}-3-[2-(dimethylamino)ethyl]-1-propylurea (compound 1-1) (10.0 g) and ethanol (200 mL) was added dropwise a mixture of 12 mol/L hydrochloric acid (3.91 mL) and ethanol (30 mL) while stirring under ice bath cooling, and the mixture was stirred at the same temperature for 3 hours. The resulting solid was collected by filtration, and washed twice with ethanol (20 mL) to give 1-{[(4aR,6R,8aR)-2-amino-3-cyano-8-methyl-4H,4aH,5H,6H,7H,8H,8aH,9H-thieno[3,2-g]quinolin-6-yl]carbonyl}-3-[2-(dimethylamino)ethyl]-1-propylurea di hydrochloride salt (11.5 g).

Workup

  1. additionwas added dropwise
  2. temperaturecooling
  3. stirringthe mixture was stirred at the same temperature for 3 hours
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed twice with ethanol (20 mL)

Sources & evidence

ORD record
ord-1fb527f43181480daf7247c50853e6d8
Source dataset
uspto-grants-2015_09
Patent number
US09138434B2

Reaction notes

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