Hydrochloric Acid → HCID 67206392, compound

HRID 1799059Notes

Reaction equation

HRID 1799059 reaction equation
C(OC([N:8]1[CH2:13][CH:12]2[CH2:14][CH:9]1[CH2:10][N:11]2[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]2[S:24][C:25]3[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=3[N:27]=2)=[CH:18][CH:17]=1)=O)(C)(C)C.[ClH:32]>C(Cl)Cl>[ClH:32].[ClH:32].[C@H:12]12[CH2:14][C@H:9]([NH:8][CH2:13]1)[CH2:10][N:11]2[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]2[S:24][C:25]3[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=3[N:27]=2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67206468HCID 67206468, compound

Product 1

HCID 67206392HCID 67206392, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(4-benzothiazol-2-ylmethyl-benzyl)-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (0.82 g, 1.9 mmol) in CH2Cl2 (19 mL) was added HCl (4.0 N in 1,4-dioxane, 7 mL) and the resulting white suspension was stirred at rt for 4 h. The reaction mixture was concentrated affording the title compound as a white solid (0.9 g, 100%). MS (ESI): mass calcd. for free amine C20H21N3S, 335.47; m/z found, 336.2 [M+H]+. 1H NMR (500 MHz, DMSO-d6): 12.09-11.07 (br m, 1H), 10.16-9.71 (br m, 2H), 8.03 (d, J=8.0 Hz, 1H), 7.96 (d, J=8.0 Hz, 1H), 7.72-7.70 (m, 2H), 7.50-7.47 (m, 3H), 7.42-7.39 (m, 1H), 4.62-4.59 (br m, 0.5H), 4.52 (br s, 2H), 4.48-4.44 (br m, 2H), 4.37-4.34 (br m, 1.5H), 3.95-3.92 (m, 1H), 3.72-3.70 (m, 1H), 3.34-3.30 (m, 2H), 2.69-2.63 (m, 0.5H), 2.48-2.43 (m, 0.5H), 2.13-2.06 (m, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-6833a487eaec40419c3efae89cb898d4
Source dataset
uspto-grants-2013_01
Patent number
US08344008B2

Reaction notes

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