Hydrochloric Acid → 1-(1,2,3,4-Tetrahydropyrazino[1,2-a]benzimidazol-8-yl)-4-[4-(trifluoromethyl)phenyl]pyridin-2(1H)-one

HRID 882065Notes

Reaction equation

[O:1]=[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]1[C:18]1[CH:37]=[CH:36][C:21]2[N:22]3[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][C:23]3=[N:24][C:20]=2[CH:19]=1.Cl>>[CH2:25]1[C:23]2=[N:24][C:20]3[CH:19]=[C:18]([N:3]4[CH:4]=[CH:5][C:6]([C:8]5[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:15])[F:16])=[CH:10][CH:9]=5)=[CH:7][C:2]4=[O:1])[CH:37]=[CH:36][C:21]=3[N:22]2[CH2:28][CH2:27][NH:26]1

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 68056088tert-Butyl 8-(2-oxo-4-(4-(trifluoromethyl)phenyl)pyridin-1(2H)-yl)-3,4-dihydropyrazino[1,2-a]benzimidazole-2(1H)-carboxylate

Product 1

HCID 575247601-(1,2,3,4-Tetrahydropyrazino[1,2-a]benzimidazol-8-yl)-4-[4-(trifluoromethyl)phenyl]pyridin-2(1H)-oneYield 53%

Procedure

tert-Butyl 8-(2-oxo-4-(4-(trifluoromethyl)phenyl)pyridin-1(2H)-yl)-3,4-dihydropyrazino[1,2-a]benzimidazole-2(1H)-carboxylate (15 mg, 0.023 mmol) was deprotected and converted to the hydrochloride according to Example 18 (step h) to provide the title compound (5 mg, 38%) as an orange solid: 1H NMR (500 MHz, DMSO-d6) δ 9.71 (s, 2H), 8.01 (d, J=8.3 Hz, 2H), 7.88 (d, J=8.3 Hz, 2H), 7.82 (d, J=7.8 Hz, 1H), 7.75 (m, 2H), 7.37 (d, J=8.4 Hz, 1H), 6.88 (s, 1H), 7.73 (d, J=7.5 Hz, 1H), 4.67 (s, 2H), 4.47-4.41 (m, 2H), 3.83-3.77 (m, 2H); ESI MS m/z 411 [M+H]+; HPLC (Method B) 91.3% (AUC), tR=12.8 min.

Sources & evidence

ORD record: ord-78675af589c3484c90883749fa7f6e3d
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993765B2

Reaction notes

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