Hydrochloric Acid → HCID 67468320, compound

HRID 2204072Notes

Reaction equation

[F:1][C:2]([F:29])([F:28])[C:3]1[N:11]2[C:6]([C:7]3([CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]3)[O:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=32)=[CH:5][CH:4]=1.O1CCOCC1.[ClH:36]>>[ClH:36].[F:29][C:2]([F:1])([F:28])[C:3]1[N:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[O:8][C:7]3([CH2:16][CH2:17][NH:18][CH2:19][CH2:20]3)[C:6]2=[CH:5][CH:4]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 312751,4-Dioxane

HCID 67465711HCID 67465711, compound

Product 1

HCID 67468320HCID 67468320, compound

Procedure

tert-Butyl 1′-(trifluoromethyl)spiro[piperidine-4,4′-pyrrolo[2,1-c][1,4]benzoxazine]-1-carboxylate (30 mg, 0.074 mmol) was dissolved in hydrogen chloride in dioxane (700 μL of 4.0 M, 2.8 mmol). The reaction mixture was allowed to stand for 20 minutes. The solvent was evaporated to give 1-(trifluoromethyl)spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine] hydrochloride was then used without further purification (25 mg, 99%). 1H NMR (400 MHz, DMSO) δ 9.23 (br s, 2H), 7.59 (d, J=8.1 Hz, 1H), 7.40-7.19 (m, 3H), 7.05 (d, J=3.9 Hz, 1H), 6.38 (d, J=4.0 Hz, 1H), 3.42-3.04 (m, 4H), 2.37-2.00 (m, 4H). ESI-MS m/z calc. 308.3, found 309.5 (M+1)+; Retention time: 1.53 minutes (3 min run).

Workup

customThe solvent was evaporated

Sources & evidence

ORD record: ord-2fc1dd488efd484ebdc2bd5188072ed2
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365588B2

Reaction notes

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