Hydrochloric Acid → HCID 67468320, compound

HRID 1907988Notes

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-88b39eeb00ab40739073acba3aceb2c4
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598164B2

Reaction notes

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