Triethylamine → HCID 178454040, 화합물

HRID 724272노트

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HRID 724272 반응식
[C:1]([O:5][C:6](=[O:15])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[F:23][C:24]1[CH:25]=[N:26][C:27]([Cl:33])=[C:28]([CH:32]=1)[C:29](O)=[O:30].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C)C=O>[C:1]([O:5][C:6](=[O:15])[NH:7][C@H:8]1[CH2:9][CH2:10][C@@H:11]([NH:14][C:29]([C:28]2[C:27]([Cl:33])=[N:26][CH:25]=[C:24]([F:23])[CH:32]=2)=[O:30])[CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2756050Cis tert-Butyl 4-aminocyclohexylcarbamateHCID 114352432-Chloro-5-fluoronicotinic acid

생성물 1

HCID 178454040HCID 178454040, 화합물수율 73.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

(4-Amino-cyclohexyl)-carbamic acid tert-butyl ester (80:20 syn:anti, 4.49 g, 20.9 mmol) was dissolved in dimethylformamide (100 ml) and triethylamine (8.34 ml, 59.8 mmol) was added followed by 5-fluoro-2-chloronicotinic acid (3.5 g, 19.9 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (4.2 g, 21.9 mmol) and 1-hydroxybenzotriazole (2.96 g, 21.9 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 (50 ml) and ethyl acetate (100 ml) and the aqueous phase was extracted with dichloromethane (2×50 ml). The combined organic extracts were concentrated under reduced pressure, re-dissolved in dichloromethane (100 ml), washed with water (50 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 ethyl acetate:pentane (2:3 changing to 1:1, by volume) to give {cis-4-[(2-Chloro-5-fluoro-pyridine-3-carbonyl)-amino]-cyclohexyl}-carbamic acid tert-butyl ester (5.44 g) as a white foam.

후처리

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was partitioned between sat. sodium bicarbonate solution (50 ml) and ethyl acetate (100 ml)
  3. extractionthe aqueous phase was extracted with dichloromethane (2×50 ml)
  4. concentrationThe combined organic extracts were concentrated under reduced pressure
  5. dissolutionre-dissolved in dichloromethane (100 ml)
  6. washwashed with water (50 ml)
  7. dry with materialdried over MgSO4
  8. customthe solvent was removed under reduced pressure
  9. customThe residue was purified by flash column chromatography on silica gel eluting with a solvent gradient of ethyl acetate:pentane (2:3 changing to 1:1, by volume)

출처 및 근거

ORD 기록
ord-0fe66ae5d12047f8a2b3a2023b4f7275
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141586B2

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