Hydrochloric Acid → HCID 86731036, compound

HRID 2280218Notes

Reaction equation

HRID 2280218 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]([CH2:28][CH3:29])[C:19]([NH:21][C@@H:22]([CH3:27])[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(OC(C)C)(C)C>CC(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]([CH2:28][CH3:29])[C:19]([NH:21][C@@H:22]([CH3:27])[CH2:23][N:24]([CH3:25])[CH3:26])=[O:20])=[O:17])[CH2:9][N:10]3[CH3:15])[CH2:5][C:4]=2[C:3]=1[C:30]#[N:31]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7914Diisopropyl EtherHCID 74223118HCID 74223118, compound2×

Product 1

HCID 86731036HCID 86731036, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

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-[(2S)-1-(dimethylamino)propan-2-yl]-1-ethylurea (compound 1-57) (0.88 g) and 2-propanol (17.6 mL) was added 12 mol/L hydrochloric acid (0.36 mL) while stirring under water bath cooling. To the solution was added dropwise diisopropyl ether (17.6 mL), and stirred at the room temperature for 1 hour, then for 1 hour under ice bath cooling. The resulting solid was collected by filtration, and washed twice with ice-cold 2-propanol/diisopropyl ether mixed solvent (2-propanol:diisopropyl ether=1:1) (4.4 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-[(2S)-1-(dimethylamino)propan-2-yl]-1-ethylurea di hydrochloride salt (0.92 g).

Workup

  1. temperaturecooling
  2. stirringstirred at the room temperature for 1 hour
  3. temperaturefor 1 hour under ice bath cooling
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed twice with ice-cold 2-propanol/diisopropyl ether mixed solvent (2-propanol:diisopropyl ether=1:1) (4.4 mL)

Sources & evidence

ORD record
ord-511bca36cfa547e6b61074975bb7b419
Source dataset
uspto-grants-2015_09
Patent number
US09138434B2

Reaction notes

Loading…