2-Chlorobenzylamine → 3-(2-methylsulfanyl-pyrimidin-4-yl)-1-oxo-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazole-2-carboxylic acid 2-chloro-benzylamide

HRID 1455252노트

반응식

HRID 1455252 반응식
[CH3:1][S:2][C:3]1[N:8]=[C:7]([C:9]2[N:13]3[CH2:14][CH2:15][CH2:16][N:12]3[C:11](=[O:17])[C:10]=2[C:18]([OH:20])=O)[CH:6]=[CH:5][N:4]=1.[Cl:21][C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[CH2:24][NH2:25].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C([O-])(O)=O.[Na+]>CN(C=O)C>[Cl:21][C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[CH2:24][NH:25][C:18]([C:10]1[C:11](=[O:17])[N:12]2[CH2:16][CH2:15][CH2:14][N:13]2[C:9]=1[C:7]1[CH:6]=[CH:5][N:4]=[C:3]([S:2][CH3:1])[N:8]=1)=[O:20]

참가 물질

7

반응물 5

HCID 666482-ChlorobenzylamineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 574380863-(2-methylsulfanyl-pyrimidin-4-yl)-1-oxo-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazole-2-carboxylic acid

생성물 1

HCID 575317953-(2-methylsulfanyl-pyrimidin-4-yl)-1-oxo-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazole-2-carboxylic acid 2-chloro-benzylamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 3-(2-methylsulfanyl-pyrimidin-4-yl)-1-oxo-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazole-2-carboxylic acid, 14, (0.23 g, 0.78 mmol) and 2-chlorobenzylamine (0.10 mL, 0.78 mmol) in DMF (3 mL) is added 1-hydroxybenzotriazole (0.21 g, 1.57 mmol) and then 1-(3-dimethylamino-propyl)-3-ethylcarbodiimide hydrochloride (0.18 g, 0.94 mmol). The reaction solution is stirred at room temperature for 6 days then poured into aqueous saturated NaHCO3. The aqueous phase is extracted with three times with EtOAc and the combined organic phases are washed with aqueous saturated NH4Cl, and H2O, dried (MgSO4), filtered and concentrated in vacuo to afford the desired product which is used without further purification: 1H NMR (300 MHz, CDCl3) δ 9.49 (bd s, NH), 8.69 (d, J=5.1 Hz, 1H), 8.16 (d, J=5.1 Hz, 1H), 7.44-7.37 (m, 2H), 7.25-7.19 (m, 2H), 4.70 (d, J=5.4 Hz, 2H), 4.41 (t, J=7.2 Hz, 2H), 4.14 (t, J=7.2 Hz, 2H), 2.78 (dd, J=7.5, 7.5, 7.5, 7.5 Hz, 2H), 2.06 (s, 3H); ESI+ MS: m/z (rel intensity) 415.9 (100, M++H).

후처리

  1. extractionThe aqueous phase is extracted with three times with EtOAc
  2. washthe combined organic phases are washed with aqueous saturated NH4Cl, and H2O
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-9ab77b3b08c4426790043a9628a995f7
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07482356B2

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