Triethylamine → HCID 19736673, 화합물

HRID 326282

반응식

HRID 326282 반응식
[NH2:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].Cl.[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1CC(O)=O.C(N(CC)CC)C.O=C1N(P(Cl)(N2CCOC2=O)=O)[CH2:35][CH2:34][O:33]1.N1C=CC=CC=1CC(O)=O>ClCCCl>[Cl:12][C:10]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([NH:1][C:34](=[O:33])[CH2:35][C:18]2[CH:19]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH:11]=1

참가 물질

7

반응물 5

HCID 8471Triethylamine2회HCID 80001Methyl 4-chloroanthranilateHCID 853172-Pyridineacetic acid, hydrochloride (1:1)HCID 853182-Pyridineacetic acidHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chloride

생성물 1

HCID 19736673HCID 19736673, 화합물

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

To a solution of methyl 2-amino-4-chlorobenzoate (2 g, 10.8 mmol) in 1,2-dichlorethane (60 ml) was added 2-pyridylacetic acid hydrochloride (1.9 g, 10.8 mmol), triethylamine (3.2 ml, 22.7 mmol) and bis (2-oxo-3-oxazolidinyl)phosphinic chloride and the reaction refluxed for 8 h. More 2-pyridylacetic acid (1.9 g, 10.8 mmol) and triethylamine (3.2 ml, 22.7 mmol) were added and refluxing continued for a further 16 h. The solvent was evaporated and the residue partitioned between saturated aqueous sodium bicarbonate solution (50 ml) and dichloromethane (50 ml). The organic phase was dried (MgSO4) and evaporated. The residue was purified by flash chromatography on silica (eluting with 50% ethyl acetate/60°-90° petrol) to afford methyl 4-chloro-2-(3-pyridyl)acetamidobenzoate as a green solid (2.5 g), m.p. 85°-87° C. To a solution of the foregoing amide (1 g, 3.3 mmol) in tetrahydrofuran (40 mml) was added a solution of potassium hexamethyldisilazide in toluene (0.5M, 16.6 ml, 8.3 mmol) and the reaction stirred for 2 h. Methanol (15 ml) was added and the solvent evaporated. The residue was partitioned between aqueous sodium hydroxide (1M, 40 ml) and diethyl ether (40 ml), and the aqueous layer acidified with hydrochloric acid (5M). The resultant precipitate was collected and recrystallised from dimethylformamide/water to afford the title compound as a yellow-green solid; m.p.>330° C. (from DMF/H2O) (Found: C, 61.48; H, 3.20; N, 10.20; C14H9ClN2O2 requires C, 61.66; H, 3.33; N, 10.27%); δH (DMSO-d6) 7.15 (1H, dd, J=8.5 Hz and 1.9 Hz, 5-H), 7.26 (1H, s, 8-H), 7.42 (1H, t, J=6.1 Hz, 5'-H), 8.02 (1H, d, J=8.5 Hz, 5-H), 8.16 (1H, t, J=7.3 Hz, 4'-H), 8.78 (1H, d, J=8.6 Hz, 6'-H), 9.38 (1H, d, J=8.8 Hz, 3'-H), 11.20 (1H, s, NH); m/z 272 (M+).

후처리

  1. temperaturethe reaction refluxed for 8 h
  2. temperaturerefluxing
  3. customThe solvent was evaporated
  4. customthe residue partitioned between saturated aqueous sodium bicarbonate solution (50 ml) and dichloromethane (50 ml)
  5. dry with materialThe organic phase was dried (MgSO4)
  6. customevaporated
  7. customThe residue was purified by flash chromatography on silica (eluting with 50% ethyl acetate/60°-90° petrol)

출처 및 근거

ORD 기록
ord-c2682c8eec7843e69178a774e2b5f3fc
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05268378

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