Hydrochloric Acid → N-{[1-[(3-Cyanophenyl)methyl]-6-hydroxy-2,4-dioxo-3-(phenylmethyl)-1,2,3,4-tetrahydro-5-pyrimidinyl]carbonyl}glycine

HRID 2410025노트

반응식

HRID 2410025 반응식
[C:1]([C:3]1[CH:4]=[C:5]([CH2:9][N:10]2[C:15]([OH:16])=[C:14]([C:17]([NH:19][CH2:20][C:21]([O:23]CC)=[O:22])=[O:18])[C:13](=[O:26])[N:12]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:11]2=[O:34])[CH:6]=[CH:7][CH:8]=1)#[N:2].OC1NC(=O)N(CC2C=CC=CC=2)C(=O)C=1C(NCC(OCC)=O)=O.C(C1C=C(C=CC=1)CBr)#N.C(=O)([O-])[O-].[Na+].[Na+].Cl>CN(C)C=O>[C:1]([C:3]1[CH:4]=[C:5]([CH2:9][N:10]2[C:15]([OH:16])=[C:14]([C:17]([NH:19][CH2:20][C:21]([OH:23])=[O:22])=[O:18])[C:13](=[O:26])[N:12]([CH2:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:11]2=[O:34])[CH:6]=[CH:7][CH:8]=1)#[N:2]

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 97249Benzonitrile, 3-(bromomethyl)-HCID 68637044Ethyl N-{[1-[(3-cyanophenyl)methyl]-6-hydr oxy-2,4-dioxo-3-(phenylmethyl)-1,2,3,4-tetrahydro-5-pyrimidinyl]carbonyl}glycinateHCID 178472773HCID 178472773, 화합물

생성물 1

HCID 68635462N-{[1-[(3-Cyanophenyl)methyl]-6-hydroxy-2,4-dioxo-3-(phenylmethyl)-1,2,3,4-tetrahydro-5-pyrimidinyl]carbonyl}glycine수율 65%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

Ethyl N-{[1-[(3-cyanophenyl)methyl]-6-hydroxy-2,4-dioxo-3-(phenylmethyl)-1,2,3,4-tetrahydro-5-pyrimidinyl]carbonyl}glycinate. A mixture of ethyl N-{[6-hydroxy-2,4-dioxo-3-(phenylmethyl)-1,2,3,4-tetrahydro-5-pyrimidinyl]carbonyl}glycinate (350 mg, 1.0 mmoles), 3-cyanobenzyl bromide (250 mg, 1.22 mmoles) and sodium carbonate (300 mg, 2.9 mmoles) in dimethylformamide (5.0 mL) was stirred under argon at 100° C. for 2 hours. The mixture was cooled, poured into 1 molar hydrochloric acid and extracted with ethyl acetate (×2). The combined extracts were washed with water and brine. Purification by preparative HPLC (acetonitrile-water-0.1% TFA, 20-100%) gave the title compound (300 mg, 65%). 1H NMR (400 MHz, DMSO-d6) δ ppm 10.12 (t, J=5.81 Hz, 1 H), 7.79 (s, 1 H), 7.71-7.76 (m, 1 H), 7.66 (d, J=8.34 Hz, 1 H), 7.54 (t, J=7.83 Hz, 1 H), 7.32 (d, J=4.29 Hz, 4 H), 7.23-7.29 (m, 1 H), 5.07 (s, 2 H), 5.03 (s, 2 H), 4.22 (d, J=6.06 Hz, 2 H), 4.15 (q, J=7.07 Hz, 2 H), 1.21 (t, J=7.20 Hz, 3 H)

후처리

  1. temperatureThe mixture was cooled
  2. extractionextracted with ethyl acetate (×2)
  3. washThe combined extracts were washed with water and brine
  4. customPurification by preparative HPLC (acetonitrile-water-0.1% TFA, 20-100%)

출처 및 근거

ORD 기록
ord-2cc2e90bb8f940e99f8ed773d46608b2
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08815884B2

반응 노트

불러오는 중…