Hydrochloric Acid → HCID 67408808, compound

HRID 515221Notes

Reaction equation

HRID 515221 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([C:14]4[CH:15]=[C:16]([CH:26]=[CH:27][CH:28]=4)[CH2:17][NH:18]C(=O)OC(C)(C)C)=[CH:13][C:8]=3[N:7]([CH3:29])[S:6]2(=[O:31])=[O:30])[CH2:3][CH2:2]1.C(Cl)[Cl:33].Cl.CCOC(C)=O>CO>[ClH:33].[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([C:14]4[CH:15]=[C:16]([CH2:17][NH2:18])[CH:26]=[CH:27][CH:28]=4)=[CH:13][C:8]=3[N:7]([CH3:29])[S:6]2(=[O:30])=[O:31])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 68245004HCID 68245004, compound

Product 1

HCID 67408808HCID 67408808, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a round bottom flask was added tert-butyl {3-[1-(cyclopropylmethyl)-3-methyl-2,2-dioxido-1,3-dihydro-2,1,3-benzothiadiazol-5-yl]benzyl}carbamate (23-1) (0.250 g, 0.564 mmol), DCM (2 mL), MeOH (2 mL), and finally a saturated solution of HCl in EtOAc (4N) (0.705 mL, 2.82 mmol). The reaction mixture was then capped and permitted to stir at room temperature for an hour at which point it was concentrated to give 1-{3-[1-(cyclopropylmethyl)-3-methyl-2,2-dioxido-1,3-dihydro-2,1,3-benzothiadiazol-5-yl]phenyl}methanamine hydrochloride (23-2) as a waxy pink solid. HRMS (M+H)+: observed=344.1429, calculated=344.1427.

Workup

  1. customThe reaction mixture was then capped
  2. concentrationwas concentrated

Sources & evidence

ORD record
ord-0022a3ac303242149a92dfee922059cd
Source dataset
uspto-grants-2015_08
Patent number
US09108937B2

Reaction notes

Loading…