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Acetic Acid → 2-[4-[[2-(5-chloro-2-thienyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl]amino]phenyl]acetic acid

HRID 1508697
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HRID 1508697 반응식
Cl[C:2]1[C:3]2[CH2:16][CH2:15][CH2:14][C:4]=2[N:5]=[C:6]([C:8]2[S:9][C:10]([Cl:13])=[CH:11][CH:12]=2)[N:7]=1.[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25]([OH:27])=[O:26])=[CH:20][CH:19]=1.CC(O)=O.C(OCC)(=O)C>Cl.O>[Cl:13][C:10]1[S:9][C:8]([C:6]2[N:7]=[C:2]([NH:17][C:18]3[CH:19]=[CH:20][C:21]([CH2:24][C:25]([OH:27])=[O:26])=[CH:22][CH:23]=3)[C:3]3[CH2:16][CH2:15][CH2:14][C:4]=3[N:5]=2)=[CH:12][CH:11]=1
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참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 145334-Aminophenylacetic acidHCID 613820204-chloro-2-(5-chlorothiophen-2-yl)-5H,6H,7H-cyclopenta[d]pyrimidine

생성물 1

HCID 742209102-[4-[[2-(5-chloro-2-thienyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl]amino]phenyl]acetic acid수율 78%

시약·촉매·용매 2

HCID 313
Hydrochloric Acid
촉매
HCID 962Water용매

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온도
100 °C

실험 절차

An 18-mL vial was charged with 4-chloro-2-(5-chloro-2-thienyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidine (30 mg, 0.11 mmol, 1.1 eq.), 2-(4-aminophenyl)acetic acid (15 mg, 0.1 mmol, 1 eq.), and AcOH (1 ml). To the mixture was added HCl (4 N in dioxane, 5 drops) The resulting mixture was stirred at 100° C. for 2 hr. After cooling to rt, the reaction mixture was diluted with addition of water. The precipitate was collected by filtration and washed with water followed by dichloromethane, The product thus obtained (30 mg, 78% yield) was further treated with ethyl acetate to afford 2-[4-[[2-(5-chloro-2-thienyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl]amino]phenyl]acetic acid (7.2 mg). MW=385.87. 1H NMR (DMSO-D6, 360 MHz) δ 9.22 (brs, 1H), 7.76 (d, J=3.9 Hz, 1H), 7.70 (d, J=8.2 Hz, 2H), 7.26 (d, J=8.2 Hz, 2H), 7.21 (d, J=3.9 Hz, 1H), 3.55 (s, 2H), 2.87 (m, 4H), 2.09 (m, 2H).

후처리

  1. temperatureAfter cooling to rt
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. customThe product thus obtained (30 mg, 78% yield)

출처 및 근거

ORD 기록
ord-19689104ccf44ea58e3109fffd165ba6
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09221843B2

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