6-Phenylnicotinic acid → HCID 57682707, 화합물

HRID 494213

반응식

HRID 494213 반응식
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][N:9]2[C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])=[CH:4][CH:3]=1.[C:18]1([C:24]2[CH:32]=[CH:31][C:27]([C:28](O)=[O:29])=[CH:26][N:25]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:18]1([C:24]2[CH:32]=[CH:31][C:27]([C:28]([NH:1][C:2]3[CH:11]=[C:10]4[C:5]([CH2:6][CH2:7][CH2:8][N:9]4[C:12](=[O:17])[C:13]([F:16])([F:14])[F:15])=[CH:4][CH:3]=3)=[O:29])=[CH:26][N:25]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

참가 물질

6

반응물 3

HCID 1201186-Phenylnicotinic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 82048422HCID 82048422, 화합물

생성물 1

HCID 57682707HCID 57682707, 화합물

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of 7-amino-1-trifluoroacetyl-1,2,3,4-tetrahydroquinoline (D5) (122 mg, 0.5 mmol) in DCM (2 ml) was added 6-phenylnicotinic acid (D48) (119 mg, 0.6 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (111 mg, 0.6 mmol) and 4-dimethylaminopyridine (7 mg, 0.06 mmol) and the reaction stirred at ambient temperature for until complete by tlc. The mixture was then washed with 2M sodium hydroxide solution (1 ml), dried over magnesium sufate and concentrated in vacuo to give the crude product which was purified by silica SPE chromatography. Elution with 20% EtOAc/60-80° C. petroleum ether gave an off-white solid which was recrystallised from EtOAc/60-80° C. petroleum ether giving the title compound as a white solid. 1H NMR (250 MHz, CDCl3) δ (ppm): 9.10 (d, 1H), 8.20 (m, 2H), 8.04 (m, 2H), 7.86 (br, 1H), 7.82 (dd, 1H), 7.72 (br, 1H), 7.50 (m, 3H), 7.19 (1H, d), 3.84 (m, 2H), 2.84 (m, 2H), 2.06 (m, 2H).

후처리

  1. washThe mixture was then washed with 2M sodium hydroxide solution (1 ml)
  2. dry with materialdried over magnesium sufate
  3. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-5b05f69c153d40d2a6b6b2d2794a6ba8
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538121B2

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