Hydrochloric Acid → HCID 86669660, compound

HRID 1623913Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH2:14][NH:15][C:16]([C:18]2[C:19]3[CH2:20][C@H:21]4[CH2:34][C@H:22]4[C:23]=3[N:24]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=3[F:33])[N:25]=2)=[O:17])[CH2:9]1)=O)(C)(C)C.Cl>O1CCOCC1>[NH:8]1[CH2:13][CH2:12][O:11][CH:10]([CH2:14][NH:15][C:16]([C:18]2[C:19]3[CH2:20][C@H:21]4[CH2:34][C@H:22]4[C:23]=3[N:24]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=3[F:33])[N:25]=2)=[O:17])[CH2:9]1

Participants

Conditions

Temperature: 23 °C

Procedure

To 2-({[(1aR,5aR)-2-(2,4-Difluoro-phenyl)-1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carbonyl]-amino}-methyl)-morpholine-4-carboxylic acid tert-butyl ester (140 mg, 0.295 mmol) was added a 4.0 M dioxane solution of HCl (2.213 mL, 8.85 mmol). The solution was stirred at 23° C. for 2.5 h then concentrated. The residue was taken up in diethyl ether (8 mL). The resulting precipitate was collected by filtration then dried under reduced pressure to provide the title compound (hydrochloride salt, 90 mg). LCMS m/z=375.1 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 0.40 (td, J=4.5, 3.4 Hz, 1H), 1.14-1.19 (m, 1H), 2.16-2.20 (m, 1H), 2.25-2.31 (m, 1H), 2.70-2.78 (m, 2H), 2.87-3.00 (m, 2H), 3.13-3.21 (m, 2H), 3.23-3.32 (m, 2H), 3.66-3.73 (m, 1H), 3.80-3.86 (m, 1H), 3.95 (dd, J=12.6, 3.1 Hz, 1H), 7.29-7.34 (m, 1H), 7.58-7.64 (m, 1H), 7.78 (td, J=8.9, 5.9 Hz, 1H), 8.17 (t, J=6.1 Hz, 1H), 9.14 (bs, 2H).

Workup

concentrationthen concentrated
filtrationThe resulting precipitate was collected by filtration
customthen dried under reduced pressure

Sources & evidence

ORD record: ord-4406c002a0db447d9e19a973c7c4ee2d
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778950B2

Reaction notes

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