p-Aminophenylacetic acid ethyl ester → HCID 71625094, compound

HRID 1509010Notes

Reaction equation

HRID 1509010 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][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:30][CH:29]=1>>[O:23]=[S:22]1(=[O:24])[C:8]2[C:7]([NH:27][C:28]3[CH:29]=[CH:30][C:31]([CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:32][CH:33]=3)=[N:12][C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[N:10][C:9]=2[CH2:19][CH2:20][CH2:21]1

Participants

3

Reactant 2

HCID 225219p-Aminophenylacetic acid ethyl esterHCID 71625093HCID 71625093, compound

Product 1

HCID 71625094HCID 71625094, compoundYield 77.1%

Procedure

Following general procedure G, 5,5-dioxido-2-phenyl-7,8-dihydro-6H-thiopyrano[3,2-d]pyrimidin-4-yl trifluoromethanesulfonate (1.0 g, 2.46 mmol) was reacted with ethyl 2-(4-aminophenyl)acetate (0.527 g, 2.94 mmol) to afford the desired product (0.83 g, 77%) as a light yellow solid. MW=437.51. 1H NMR (DMSO-d6, 500 MHz) δ 8.77 (s, 1H), 8.28-8.24 (m, 2H), 7.64-7.49 (m, 5H), 7.34 (d, J=8.5 Hz, 2H), 4.10 (q, J=7.0 Hz, 2H), 3.76-3.72 (m, 2H), 3.70 (s, 2H), 3.08 (t, J=6.5 Hz, 2H), 2.43-2.35 (m, 2H), 1.20 (t, J=7.0 Hz, 3H); APCI MS m/z 438 [M+H]+.

Sources & evidence

ORD record
ord-c581745378b648a3ad03882e2d4e1bde
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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