Hydrochloric Acid → HCID 54577789, compound

HRID 1845907Notes

Reaction equation

HRID 1845907 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:32]=[CH:31][C:12]2[N:13]([CH2:17][CH:18]3[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]3)[C:14](=[O:16])[S:15][C:11]=2[CH:10]=1)#[N:2].CO.Cl.CCOC(C)=O>C(Cl)Cl>[O:16]=[C:14]1[N:13]([CH2:17][CH:18]2[CH2:19][CH2:20][NH:21][CH2:22][CH2:23]2)[C:12]2[CH:31]=[CH:32][C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[C:1]#[N:2])=[CH:10][C:11]=2[S:15]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 8857Ethyl AcetateHCID 67462346HCID 67462346, compound

Product 1

HCID 54577789HCID 54577789, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a round bottom flask was added tert-butyl 4-{[6-(2-cyanophenyl)-2-oxo-1,3-benzothiazol-3(2H)-yl]methyl}piperidine-1-carboxylate (11-2) (0.242 g, 0.538 mmol), MeOH (2.5 mL), DCM (2.5 mL), and a sat'd solution of HCl in EtOAc (˜4N) (1.346 mL, 5.38 mmol). The reaction mixture was capped and permitted to stir for two hours then concentrated to give 2-[2-oxo-3-(piperidin-4-ylmethyl)-2,3-dihydro-1,3-benzothiazol-6-yl]benzonitrile (11-3) as a tan solid. HRMS (M+H)+: observed=350.1322, calculated=350.1322.

Workup

  1. customThe reaction mixture was capped
  2. concentrationthen concentrated

Sources & evidence

ORD record
ord-7671d4d9b87d4a358772a73d7a054d97
Source dataset
uspto-grants-2015_02
Patent number
US08952005B2

Reaction notes

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