4-Aminophenethyl alcohol → HCID 90112006, compound

HRID 1509008Notes

Reaction equation

HRID 1509008 reaction equation
FC(F)(F)S(O[C:7]1[C:8]2[S:22](=[O:24])(=[O:23])[CH2:21][CH2:20][CH2:19][C:9]=2[N:10]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:12]=1)(=O)=O.[NH2:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][OH:36])=[CH:30][CH:29]=1>>[OH:36][CH2:35][CH2:34][C:31]1[CH:32]=[CH:33][C:28]([NH:27][C:7]2[C:8]3[S:22](=[O:24])(=[O:23])[CH2:21][CH2:20][CH2:19][C:9]=3[N:10]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:12]=2)=[CH:29][CH:30]=1

Participants

3

Reactant 2

HCID 669044-Aminophenethyl alcoholHCID 71625093HCID 71625093, compound

Product 1

HCID 90112006HCID 90112006, compoundYield 68.3%

Procedure

Following general procedure G, 5,5-dioxido-2-phenyl-7,8-dihydro-6H-thiopyrano[3,2-d]pyrimidin-4-yl trifluoromethanesulfonate (0.123 g, 0.30 mmol) was reacted with 2-(4-aminophenyl)ethanol (0.045 g, 0.33 mmol) to afford the desired product (0.081 g, 68%) as a light yellow solid. MW=395.47. 1H NMR (DMSO-d6, 500 MHz) δ 8.72 (s, 1H), 8.29-8.25 (m, 2H), 7.61-7.49 (m, 5H), 7.30 (d, J=8.5 Hz, 2H), 4.65 (t, J=5.5 Hz, 1H), 3.76-3.71 (m, 2H), 3.67-3.61 (m, 2H), 3.07 (t, J=6.5 Hz, 2H), 2.75 (t, J=7.0 Hz, 2H), 2.43-2.35 (m, 2H); APCI MS m/z 396 [M+H]+.

Sources & evidence

ORD record
ord-72ebf8c9ac57423aa2dbfed3ea1e5dd3
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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