Hydrochloric Acid → HCID 67207078, compound

HRID 384515Notes

Reaction equation

HRID 384515 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]([N:11]1[CH2:16][C@H:15]2[CH2:17][C@@H:12]1[CH2:13][N:14]2[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][C:26]2[S:27][C:28]3[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=3[N:30]=2)=[CH:21][CH:20]=1)=[O:10])(C)(C)C.Cl>C(Cl)Cl>[NH2:7][CH2:8][C:9]([N:11]1[CH2:16][C@H:15]2[CH2:17][C@@H:12]1[CH2:13][N:14]2[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][C:26]2[S:27][C:28]3[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=3[N:30]=2)=[CH:21][CH:20]=1)=[O:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67205977HCID 67205977, compound

Product 1

HCID 67207078HCID 67207078, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of (R,R)-(2-{5-[4-(benzothiazol-2-yloxy)-benzyl]-2,5-diaza-bicyclo[2.2.1]hept-2-yl}-2-oxo-ethyl)-carbamic acid tert-butyl ester (8.2 mg, 0.02 mmol) in CH2Cl2 (0.3 mL) was added HCl (4.0 N in 1,4-dioxane, 0.3 mL). The solution was stirred for 2 h and concentrated under a stream of dry nitrogen. Purification via preparative reverse phase HPLC afforded the title compound (2.7 mg, 38%). MS (ESI): mass calcd. for C21H22N4O2S, 394.15; m/z found, 395.1 [M+H]+. 1H NMR (400 MHz, CDCl3, mixture of rotamers): 7.74 (d, J=8.1 Hz, 1H), 7.67 (d, J=7.9 Hz, 1H), 7.44-7.36 (m, 3H), 7.34-7.28 (m, 2H), 7.28-7.23 (m, 1H), 4.81 (s, 0.5H), 4.21 (s, 0.5H), 3.81-3.72 (m, 2.5H), 3.58 (s, 1H), 3.54-3.46 (m, 1H), 3.39-3.24 (m, 2.5H), 3.00 (dd, J=9.6, 2.0 Hz, 0.5H), 2.86 (dd, J=9.7, 2.1 Hz, 0.5H), 2.76 (d, J=9.8 Hz, 0.5H), 2.67-2.58 (m, 0.25H), 2.54 (d, J=9.6 Hz, 0.5H), 2.00 (d, J=9.6 Hz, 0.5H), 1.93 (d, J=9.9 Hz, 0.5H), 1.86-1.30 (m, 2.75H).

Workup

  1. concentrationconcentrated under a stream of dry nitrogen
  2. customPurification via preparative reverse phase HPLC

Sources & evidence

ORD record
ord-a0fb70c414a7424884ee9d823e2d1d1e
Source dataset
uspto-grants-2013_02
Patent number
US08367719B2

Reaction notes

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