Hydrochloric Acid → HCID 66674618, compound

HRID 1691414Notes

Reaction equation

HRID 1691414 reaction equation
C(OC(=O)[NH:7][C@H:8]1[C@H:17]([O:18][CH3:19])[CH2:16][C:15]2[C:10](=[CH:11][C:12]([C:20](=[O:22])[NH2:21])=[CH:13][CH:14]=2)[C:9]1([CH3:24])[CH3:23])(C)(C)C.[ClH:26].O1CCOCC1>C(Cl)Cl>[ClH:26].[NH2:7][CH:8]1[C:9]([CH3:24])([CH3:23])[C:10]2[CH:11]=[C:12]([C:20]([NH2:21])=[O:22])[CH:13]=[CH:14][C:15]=2[CH2:16][CH:17]1[O:18][CH3:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 66674845HCID 66674845, compound

Product 1

HCID 66674618HCID 66674618, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a slurry of trans-(7-carbamoyl-3-methoxy-1,1-dimethyl-1,2,3,4-tetrahydro-naphthalen-2-yl)-carbamic acid tert-butyl ester (9.22 g, 26.4 mmol) in DCM (100 mL) was added 4 N HCl in dioxane (25 mL, 100 mmol) slowly. The reaction mixture was stirred at RT for 15 h, concentrated to dryness, triturated with DCM (25 mL) for 30 min, filtered, rinsed with DCM (3×15 mL), and dried under vacuum. Ethanol (100 mL) was added and the reaction mixture was concentrated under vacuum to give the HCl salt of the title compound (7.17 g) as a white powder. (m/z): [M+H]+ calcd for C14H20N2O2 249.16; found 249.1. 1H NMR (d6-DMSO, 400 mHz) δ (ppm): 8.18 (s, 3H), 8.00 (s, 1H), 7.92 (d, J=1.6 Hz, 1H), 7.66 (dd, J=8.0 Hz, 1.8 Hz, 1H), 7.32 (s, 1H), 7.17 (d, J=8.0 Hz, 1H), 3.70 (m, 1H), 3.44 (s, 3H), 3.43 (m, 1H), 3.22 (m, 1H), 2.67 (dd, J=16.4 Hz, 10.2 Hz), 1.50 (s, 3H), 1.24 (s, 3H).

Workup

  1. concentrationconcentrated to dryness
  2. customtriturated with DCM (25 mL) for 30 min
  3. filtrationfiltered
  4. washrinsed with DCM (3×15 mL)
  5. customdried under vacuum
  6. additionEthanol (100 mL) was added
  7. concentrationthe reaction mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-27f9357fd8bd465ea517f38a85e38c91
Source dataset
uspto-grants-2012_04
Patent number
US08153686B2

Reaction notes

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