6-Phenylnicotinic acid → HCID 44415813, 화합물

HRID 494211

반응식

HRID 494211 반응식
[C:1]1([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[NH2:39][C:40]1[CH:49]=[C:48]2[C:43]([CH2:44][CH2:45][CH2:46][N:47]2[CH3:50])=[CH:42][CH:41]=1>C(Cl)Cl>[CH3:50][N:47]1[C:48]2[C:43](=[CH:42][CH:41]=[C:40]([NH:39][C:11](=[O:13])[C:10]3[CH:14]=[CH:15][C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[N:8][CH:9]=3)[CH:49]=2)[CH2:44][CH2:45][CH2:46]1

참가 물질

6

반응물 4

HCID 1201186-Phenylnicotinic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 112174211-Methyl-1,2,3,4-tetrahydroquinolin-7-amine

생성물 1

HCID 44415813HCID 44415813, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 6-phenylnicotinic acid (D48) (500 mg, 2.51 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (963 mg, 5.03 mmol) and 1-hydroxybenzotriazole hydrate (340 mg, 2.51 mmol) in DCM (20 ml) was added a solution of 7-amino-1-methyl-1,2,3,4-tetrahydroquinoline (D3) (407 mg, 2.51 mmol) in DCM (5 ml). The reaction mixture was stirred overnight then washed with sat. aq. sodium hydrogen carbonate solution (2×20 ml) and brine (20 ml). The organics were dried over MgSO4 and concentrated in vacuo to give the crude product which was purified by flash column chromatography. Elution with 10-20% EtOAc/DCM gave the title compound as a yellow solid. 1H NMR (250 MHz, CDCl3) δ (ppm): 9.14 (d, 1H), 8.25 (dd, 1H), 8.07 (m, 2H), 7.85 (d, 1H), 7.71 (br, 1H), 7.48 (m, 3H), 7.03 (br, 1H), 6.93 (d, 1H), 6.75 (dd, 1H), 3.25 (m, 2H), 2.93 (s, 3H), 2.75 (t, 2H), 1.98 (m, 2H).

후처리

  1. washthen washed with sat. aq. sodium hydrogen carbonate solution (2×20 ml) and brine (20 ml)
  2. dry with materialThe organics were dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customto give the crude product which
  5. customwas purified by flash column chromatography
  6. washElution with 10-20% EtOAc/DCM

출처 및 근거

ORD 기록
ord-f8ab167295d54e7282131a11e006efac
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538121B2

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