6-Phenylnicotinic acid → HCID 44415813、化合物

HRID 494211ノート

反応式

HRID 494211 の反応式
[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

参加物

6

反応物 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

生成物 1

HCID 44415813HCID 44415813、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f8ab167295d54e7282131a11e006efac
出典データセット
uspto-grants-2009_05
特許番号
US07538121B2

反応ノート

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