Hydrochloric Acid → HCID 10304683, compound

HRID 489663Notes

Reaction equation

HRID 489663 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C@@H:10]([NH:30][C:31]([C@@H:33]2[CH2:42][C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH2:35][N:34]2C(OC(C)(C)C)=O)=[O:32])[C:11]([N:13]2[CH2:18][CH2:17][CH:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[CH2:15][CH2:14]2)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].Cl>CCOC(C)=O>[CH2:35]1[C:36]2[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:42][C@@H:33]([C:31]([NH:30][C@H:10]([CH2:9][C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[C:11]([N:13]2[CH2:14][CH2:15][CH:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[NH:25][S:26]([CH3:29])(=[O:27])=[O:28])[CH2:17][CH2:18]2)=[O:12])=[O:32])[NH:34]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69740438HCID 69740438, compound

Product 1

HCID 10304683HCID 10304683, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 150 mL round-bottomed flask equipped with stirring was added tert-butyl(3S)-3-(N-[(1R)-1-[(3,4-dichlorophenyl)methyl]-2-(4-{2-[(methylsulfonyl)-amino]phenyl)piperidyl)-2-oxoethyl]carbamoyl}-1,2,3,4-tetrahydroisoquinoline-2-carboxylate (Step b) (0.54 g, 0.74 mmol) followed by a saturated soln of HCl in EtOAc (50 mL). The reaction mixture was stirred at RT for 1 h and concentrated in vacuo to a white solid. Recrystallization from MeOH:Et2O (1:20) provided the title compound (HCl salt) as a white solid (0.3 g). MP 181° C. (decomposed). MS (ESI, pos. ion) m/z: 629 (M+1); MS (ESI, neg. ion) m/z: 627 (M−1). Calc'd for C31H34Cl2N4O4S: 628.17. Anal. Calcd for C31H34Cl2N4O4S.HC].H2O: C, 51.71; H, 5.74; N, 7.78; Cl, 14.77. Found: C, 51.66; H, 5.39; N, 7.49; Cl, 15.07.

Workup

  1. customTo a 150 mL round-bottomed flask equipped
  2. stirringThe reaction mixture was stirred at RT for 1 h
  3. concentrationconcentrated in vacuo to a white solid
  4. customRecrystallization from MeOH:Et2O (1:20)

Sources & evidence

ORD record
ord-ef9a66dfc64d48548db857f59913ac34
Source dataset
uspto-grants-2005_12
Patent number
US06977264B2

Reaction notes

Loading…