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1,1'-Carbonyldiimidazole → (R)-N-(1-(3,4-dichlorophenyl)ethyl)-2-(2-ethoxypyridin-4-ylamino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxamide

HRID 2279497
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HRID 2279497 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([NH2:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[Cl:8].C1N=CN([C:17](N2C=NC=C2)=[O:18])C=1.[CH2:24]([O:26][C:27]1[CH:32]=[C:31]([NH:33][C:34]2[N:35]=[CH:36][C:37]3[CH2:43][CH2:42][NH:41][CH2:40][C:38]=3[N:39]=2)[CH:30]=[CH:29][N:28]=1)[CH3:25].CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([NH:11][C:17]([N:41]2[CH2:42][CH2:43][C:37]3[CH:36]=[N:35][C:34]([NH:33][C:31]4[CH:30]=[CH:29][N:28]=[C:27]([O:26][CH2:24][CH3:25])[CH:32]=4)=[N:39][C:38]=3[CH2:40]2)=[O:18])[CH3:10])[CH:5]=[CH:6][C:7]=1[Cl:8]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 793515(R)-1-(3,4-dichlorophenyl)ethanamineHCID 68294219N-(2-ethoxypyridin-4-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-amine

생성물 1

HCID 60198529(R)-N-(1-(3,4-dichlorophenyl)ethyl)-2-(2-ethoxypyridin-4-ylamino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxamide

시약·촉매·용매

1
HCID 6344Dichloromethane용매

실험 절차

A vial was charged with 185 (0.105 g, 0.553 mmol), CDI (0.0896 g, 0.553 mmol) and DCM (2 mL) and stirred for 30 min. To the solution was added 186 (0.150 g, 0.553 mmol) and DIPEA (0.193 ml, 1.11 mmol) and the resulting reaction stirred for 3 d. The reaction was washed with brine (4 mL), and the organic phase concentrated and loaded on to a preparative SiO2 plate (1.0 mm thickness) which was developed with EtOAc/MeOH (95:5) and eluted to afford 0.038 g (13%) of I-35: 1H NMR (400 MHz, CDCl3) δ 8.23 (s, 1H), 7.96 (d, 1H), 7.73 (s, 1H), 7.44 (m, 1H), 7.35 (d, 1H), 7.29 (m, 1H), 7.20 (m, 1H), 6.95 (m, 1H), 5.40 (d, 1H), 5.00 (m, 1H), 4.49 (s, 1H), 4.36 (q, 2H), 3.68 (m, 2H), 2.72 (d, 2h), 1.49 (d, 3H), 1.39 (t, 3H); m/z (APCI-pos) M+1=487.2.

후처리

  1. customthe resulting reaction
  2. stirringstirred for 3 d
  3. washThe reaction was washed with brine (4 mL)
  4. concentrationthe organic phase concentrated
  5. washeluted
  6. customto afford 0.038 g (13%) of I-35: 1H NMR (400 MHz, CDCl3) δ 8.23 (s, 1H), 7.96 (d, 1H), 7.73 (s, 1H), 7.44 (m, 1H), 7.35 (d, 1H), 7.29 (m, 1H), 7.20 (m, 1H), 6.95 (m, 1H), 5.40 (d, 1H), 5.00 (m, 1H), 4.49 (s, 1H), 4.36 (q, 2H), 3.68 (m, 2H), 2.72 (d, 2h), 1.49 (d, 3H), 1.39 (t, 3H)

출처 및 근거

ORD 기록
ord-02e1721bff334693b486ee6ffa3edb30
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09133187B2

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