Hydrochloric Acid → HCID 69655944, compound

HRID 857793Notes

Reaction equation

HRID 857793 reaction equation
Cl.C(OC([NH:9][C@H:10]([CH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1)[C:11]([N:13]1[CH2:34][CH2:33][CH2:32][C@H:14]1[C:15]([NH:17][CH2:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1[C:26]1[C:30](Cl)=[N:29][S:28][N:27]=1)=[O:16])=[O:12])=O)(C)(C)C>C(Cl)Cl>[ClH:25].[NH2:9][C@H:10]([CH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1)[C:11]([N:13]1[CH2:34][CH2:33][CH2:32][C@H:14]1[C:15]([NH:17][CH2:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1[C:26]1[CH:30]=[N:29][S:28][N:27]=1)=[O:16])=[O:12]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69656109HCID 69656109, compound

Product 1

HCID 69655944HCID 69655944, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

HCl gas was bubbled through a stirred 0° C. solution of 1-{(2R)-2-[(tert-butoxycarbonyl)amino]-2-cyclohexylethanoyl}-N-[5-chloro-2-(4-chloro-1,2,5-thiadiazol-3-yl)benzyl]-L-prolinamide (41.1 mg, 0.07 mmol) in CH2Cl2 (1.0 mL) for 15 min. The solution was reduced in vacuo. The resulting solid was triturated with EtOAc and filtered. 1-[(2R)-2-Amino-2-cyclohexylethanoyl]-N-[5-chloro-2-(1,2,5-thiadiazol-3-yl)benzyl]-L-prolinamide hydrochloride was isolated as a solid. 1H NMR (CD3OD 400 MHz) δ 1.30 (m, 6H), 1.74 (m, 2H), 1.86 (m, 4H), 2.02 (m, 2H), 2.23 (m, 1H), 3.62 (m, 1H), 3.75 (m,1H), 3.98 (d, J=6.0 Hz, 1H), 4.42 (m, 1H), 4.64 (s, 2H), 7.46 (dd, J=2.2, 8.2 Hz, 1H), 7.62 (s, 1H), 7.74 (d, J=8.2 Hz, 1H), 8.99 (s, 1H): MS m/z=462.6.

Workup

  1. customThe resulting solid was triturated with EtOAc
  2. filtrationfiltered

Sources & evidence

ORD record
ord-48d2240c96b148ac94a8114f5ecd0052
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

Loading…