1,2-Dichloroethane → 5'-chloro-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-carboxylic acid, methoxy-methyl-amide

HRID 579591ノート

反応式

HRID 579591 の反応式
C(Cl)CCl.Cl.[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]2[CH2:18][CH2:17][CH:16]([C:19]([OH:21])=O)[CH2:15][CH2:14]2)=[N:11][CH:12]=1.C1C=CC2N(O)N=NC=2C=1.Cl.[CH3:33][NH:34][O:35][CH3:36].C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl.O>[CH3:36][O:35][N:34]([CH3:33])[C:19]([CH:16]1[CH2:15][CH2:14][N:13]([C:10]2[CH:9]=[CH:8][C:7]([Cl:6])=[CH:12][N:11]=2)[CH2:18][CH2:17]1)=[O:21]

参加物

9

反応物 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 457922471-(5-Chloropyridin-2-yl)piperidine-4-carboxylic acid hydrochloride

生成物 1

HCID 458195565'-chloro-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-carboxylic acid, methoxy-methyl-amide

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

EDC (1.61 g, 8.4 mmol) was added portionwise to a stirred solution of 5′-chloro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carboxylic acid hydrochloride (1.16 g, 4.19 mmol), DMAP (5 mg), HOBt (5 mg) and N,O-dimethylhydroxylamine hydrochloride (818 mg, 8.4 mmol) in dichloromethane (20 mL). Triethylamine (1.69 g, 2.33 mL, 16.8 mmol) was added dropwise, and the reaction mixture was stirred at room temperature overnight. The resulting solution was poured into water and extracted with ethyl acetate (3×). The combined organic phase was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give 5′-chloro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carboxylic acid, methoxy-methyl-amide as a white solid (1.05 g. 86%); 1H NMR (CDCl3, 300 MHz) δ 8.05 (d, J=2.5 Hz, 1H), 7.36 (dd, J1=9.0 Hz, J2=2.5 Hz, 1H), 6.57 (d, J=9.0 Hz, 1H), 4.25 (dt, J1=13.0 Hz, J2=3.0 Hz, 1H), 3.69 (s, 3H), 3.16 (s, 3H), 2.88 (m, 3H), and 1.78 (m, 4H); MS (+CI): m/z for C13H18ClN3O2: expected 283.1. found 284.2 (M+H)+.

後処理

  1. extractionextracted with ethyl acetate (3×)
  2. washThe combined organic phase was washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-72991b570bbe4c87a856a7bbf76d79d2
出典データセット
uspto-grants-2015_05
特許番号
US09040703B2

反応ノート

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