Triethylamine → HCID 178503265, 화합물

HRID 724308

반응식

HRID 724308 반응식
[CH3:1][S:2][C:3]1[CH:18]=[CH:17][C:6]([O:7][C:8]2[N:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([OH:12])=O)=[CH:5][CH:4]=1.C(N(CC)CC)C.Cl.[NH2:27][C@@H:28]1[CH2:33][CH2:32][C@H:31]([OH:34])[CH2:30][CH2:29]1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C)C=O>[NH3:16].[OH:34][C@@H:31]1[CH2:32][CH2:33][C@H:28]([NH:27][C:10](=[O:12])[C:9]2[CH:13]=[CH:14][CH:15]=[N:16][C:8]=2[O:7][C:6]2[CH:5]=[CH:4][C:3]([S:2][CH3:1])=[CH:18][CH:17]=2)[CH2:29][CH2:30]1

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 218771372-(4-Methylsulfanyl-phenoxy)-nicotinic acidHCID 178479277HCID 178479277, 화합물

생성물 2

HCID 222AmmoniaHCID 178503265HCID 178503265, 화합물수율 181.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

2-(4-Methylsulfanyl-phenoxy)-nicotinic acid (500 mg, 1.91 mmol) was dissolved in dimethylformamide (10 ml) and triethylamine (800 μl, 5.74 mmol) was added followed by cis-4-aminocyclohexanol hydrochloride (290 mg, 1.91 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (404 mg, 2.10 mmol) and 1-hydroxybenzotriazole (284 mg, 2.10 mmol). The reaction was stirred under nitrogen at room temperature for 18 h and the solvent was removed under reduced pressure. The residue was partitioned between sat. sodium bicarbonate solution (25 ml) and ethyl acetate (20 ml) and the aqueous phase was extracted with ethyl acetate (2×20 ml). The combined organic extracts were washed with water (10 ml), brine (10 ml), dried over MgSO4 and the solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with a solvent gradient of dichloromethane:methanol:concentrated aqueous ammonia (97.5:2.5:0.25 changing to 97:3:0.3, by volume) to give N-(cis-4-hydroxy-cyclohexyl)-2-(4-methylsulfanyl-phenoxy)-nicotinamide (620 mg) as a white solid.

후처리

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was partitioned between sat. sodium bicarbonate solution (25 ml) and ethyl acetate (20 ml)
  3. extractionthe aqueous phase was extracted with ethyl acetate (2×20 ml)
  4. washThe combined organic extracts were washed with water (10 ml), brine (10 ml)
  5. dry with materialdried over MgSO4
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by flash column chromatography on silica gel eluting with a solvent gradient of dichloromethane

출처 및 근거

ORD 기록
ord-d69468b24ee649bd9f4183ae2642de3b
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141586B2

연결된 노트

불러오는 중…