Hydrochloric Acid → HCID 66580977, compound

HRID 1521822Notes

Reaction equation

O=[C:2]([CH:8]1[C:17](=O)[C:16]2[C:11](=[CH:12][C:13]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:14][CH:15]=2)[S:10][CH2:9]1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].C(OC([NH:31][NH:32][CH:33]1[CH2:38][CH2:37][CH2:36][N:35](C(OC(C)(C)C)=O)[CH2:34]1)=O)(C)(C)C.Cl>CCO>[NH:35]1[CH2:36][CH2:37][CH2:38][CH:33]([N:32]2[C:17]3[C:16]4[CH:15]=[CH:14][C:13]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:12][C:11]=4[S:10][CH2:9][C:8]=3[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[N:31]2)[CH2:34]1

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of ethyl oxo[4-oxo-7-(trifluoromethoxy)-3,4-dihydro-2H-thiochromen-3-yl]acetate (3.00 g; 8.61 mmol; 1 eq.) and tert-butyl 3-[2-(tert-butoxycarbonyl)hydrazino]piperidine-1-caroxylate (4.08 g; 12.92 mmol; 1.50 eq.) in EtOH (80 ml) is added HCl (4M in dioxane, 42.38 mL) were added in a dropwise fashion. Reaction mixture is heated at 75° C. for 5 h after which it is concentrated under vacuum, partitioned between NaHCO3 sat (pH 7-8) and EtOAc. Organic layer is washed NaHCO3 sat and brine, dried over MgSO4 to give 3.1 g (88%) of the title compound as a brown solid. 1H NMR (DMSO, 300 MHz): δ 7.77 (d, J=9.43 Hz, 1H), 7.62 (s, 1H), 7.39 (d, J=7.7 Hz, 1H), 4.61-4.46 (m, 1H), 4.40-4.26 (m, 2H), 4.17 (s, 1H), 4.09-3.98 (m, 1H), 3.19-3.06 (m, 1H), 2.97-2.82 (m, 2H), 2.17-2.05 (m, 2H), 1.99 (s, 1H), 1.80-1.67 (m, 1H), 1.67-1.45 (m, 1H), 1.32 (t, J=7.0 Hz, 3H), 1.18 (t, J=6.9 Hz, 1H).

Workup

additionwere added in a dropwise fashion
customReaction mixture
concentrationis concentrated under vacuum
custompartitioned between NaHCO3
washOrganic layer is washed NaHCO3
dry with materialbrine, dried over MgSO4

Sources & evidence

ORD record: ord-8eeda42644934f99b9b4843451f8ded7
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073940B2

Reaction notes

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