Hydrochloric Acid → N-(5',6'-dioxo-5',6'-dihydrospiro[cyclohexane-1,2'-naphtho[1,2-b][1,4]oxathiin]-4-yl)-3-(trifluoromethyl)benzamide

HRID 1665305Notes

Reaction equation

HRID 1665305 reaction equation
Cl.[NH2:2][CH:3]1[CH2:23][CH2:22][C:6]2([O:11][C:10]3[C:12]4[C:17]([C:18](=[O:21])[C:19](=[O:20])[C:9]=3[S:8][CH2:7]2)=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH2:5][CH2:4]1.[F:24][C:25]([F:36])([F:35])[C:26]1[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=1)[C:29](Cl)=[O:30].Cl>C(N(CC)CC)C>[O:20]=[C:19]1[C:9]2[S:8][CH2:7][C:6]3([CH2:22][CH2:23][CH:3]([NH:2][C:29](=[O:30])[C:28]4[CH:32]=[CH:33][CH:34]=[C:26]([C:25]([F:24])([F:35])[F:36])[CH:27]=4)[CH2:4][CH2:5]3)[O:11][C:10]=2[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:18]1=[O:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 674389234-Aminospiro[cyclohexane-1,2'-naphtho[1,2-b][1,4]oxathiine]-5',6'-dione hydrochloride

Product 1

HCID 57662013N-(5',6'-dioxo-5',6'-dihydrospiro[cyclohexane-1,2'-naphtho[1,2-b][1,4]oxathiin]-4-yl)-3-(trifluoromethyl)benzamide

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Compound 70 was synthesized using 4-aminospiro[cyclohexane-1,2′-naphtho[1,2-b][1,4]oxathiine]-5′,6′-dione hydrochloride, 3-(trifluoromethyl)benzoyl chloride, triethylamine to neutralize the hydrochloride and conditions outlined in procedure N. M.p.=266-267° C.; 400 MHz 1H NMR (DMSO-d6) δ: 8.66 (d, J=7.8 Hz, 1H), 8.21-8.16 (m, 2H), 7.92 (d, J=7.4 Hz, 1H), 7.85 (t, J=7.1 Hz, 1H), 7.80 (t, J=7.1 Hz, 1H), 7.74 (t, J=7.1 Hz, 1H), 7.58 (t, J=7.1 Hz, 1H), 4.08-3.94 (m, 1H), 3.06 (s, 2H), 2.20-2.10 (m, 2H), 1.94-1.72 (m, 7H), LCMS: 488 [M+H].

Sources & evidence

ORD record
ord-4f161a8652ec433a8fb3b5e0630cf102
Source dataset
uspto-grants-2011_10
Patent number
US08039503B2

Reaction notes

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