2-(4-Aminophenyl)acetamide → 2-(4-((2-cyclopentyl-7,8-dihydro-6H-thiopyrano[3,2-d]pyrimidin-4-yl)amino)phenyl)acetamide

HRID 1509031Notes

Reaction equation

HRID 1509031 reaction equation
FC(F)(F)S(O[C:7]1[C:8]2[S:21][CH2:20][CH2:19][CH2:18][C:9]=2[N:10]=[C:11]([CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[N:12]=1)(=O)=O.[NH2:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][C:32]([NH2:34])=[O:33])=[CH:27][CH:26]=1>>[CH:13]1([C:11]2[N:12]=[C:7]([NH:24][C:25]3[CH:26]=[CH:27][C:28]([CH2:31][C:32]([NH2:34])=[O:33])=[CH:29][CH:30]=3)[C:8]3[S:21][CH2:20][CH2:19][CH2:18][C:9]=3[N:10]=2)[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

3

Reactant 2

HCID 2380342-(4-Aminophenyl)acetamideHCID 903386872-cyclopentyl-7,8-dihydro-6H-thiopyrano[3,2-d]pyrimidin-4-yl trifluoromethanesulfonate

Product 1

HCID 903386352-(4-((2-cyclopentyl-7,8-dihydro-6H-thiopyrano[3,2-d]pyrimidin-4-yl)amino)phenyl)acetamideYield 54.3%

Procedure

Following general procedure H, 2-cyclopentyl-7,8-dihydro-6H-thiopyrano[3,2-d]pyrimidin-4-yl trifluoromethanesulfonate (0.133 g, 0.36 mmol) was reacted with 2-(4-aminophenyl)acetamide (0.063 g, 0.43 mmol) to afford the title compound (0.072 g, 54%) as an off-white solid. MW=368.50. 1H NMR (DMSO-d6, 300 MHz) δ 7.91 (s, 1H), 7.59 (d, J=8.5 Hz, 2H), 7.44 (s, 1H), 7.16 (d, J=8.5 Hz, 2H), 3.31 (s, 2H), 3.13-3.07 (m, 2H), 3.00 (quin, J=8.0 Hz, 1H), 2.75 (t, J=6.5 Hz, 2H), 2.17-2.06 (m, 2H), 1.97-1.48 (m, 8H); APCI MS m/z 369 [M+H]+.

Sources & evidence

ORD record
ord-d213c1985000428a850483559dc5114c
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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