p-Aminophenylacetic acid ethyl ester → HCID 90113089, compound

HRID 1508947Notes

Reaction equation

HRID 1508947 reaction equation
Cl[C:2]1[C:3]2[CH2:16][CH2:15][CH2:14][C:4]=2[N:5]=[C:6]([O:8][CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[N:7]=1.[CH2:17]([O:19][C:20](=[O:29])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=1)[CH3:18]>>[CH:9]1([O:8][C:6]2[N:7]=[C:2]([NH:28][C:25]3[CH:24]=[CH:23][C:22]([CH2:21][C:20]([O:19][CH2:17][CH3:18])=[O:29])=[CH:27][CH:26]=3)[C:3]3[CH2:16][CH2:15][CH2:14][C:4]=3[N:5]=2)[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

3

Reactant 2

HCID 225219p-Aminophenylacetic acid ethyl esterHCID 90111371HCID 90111371, compound

Product 1

HCID 90113089HCID 90113089, compoundYield 93%

Procedure

Following General Procedure B2, 4-chloro-2-(cyclopentyloxy)-6,7-dihydro-5H-cyclopenta[d]pyrimidine (0.075 g, 0.31 mmol) was reacted with 4-aminophenylacetic acid ethyl ester (0.084 g, 0.47 mmol) to afford the title compound (0.110 g, crude) as a white solid. MW=381.47. 1H NMR (CD3OD, 300 MHz) δ 7.61 (d, J=8.6 Hz, 2H), 7.18 (d, J=8.6 Hz, 2H), 5.55-5.45 (m, 1H), 4.13 (q, J=7.6 Hz, 2H), 3.57 (s, 2H), 2.79 (t, J=7.6 Hz, 2H), 2.71 (t, J=7.6 Hz, 2H), 2.14-1.95 (m, 4H), 1.89 (s, 1H), 1.87-1.76 (m, 4H), 1.72-1.61 (m, 2H), 1.24 (t, J=7.1 Hz, 1H); APCI MS m/z 382 [M+H]+.

Sources & evidence

ORD record
ord-e8578b4e2edd426cb8eb14c989dd9038
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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