4-Methylmorpholine → rac-8-[(2,6-Difluorobenzyl)oxy]-N-[2-hydroxy-1-(pyridin-3-yl)ethyl]-2-methylimidazo[1,2-a]-pyridine-3-carboxamide

HRID 1624127노트

반응식

HRID 1624127 반응식
[F:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([C:16](O)=[O:17])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1.F[B-](F)(F)F.N1(O[C+](N(C)C)N(C)C)C2C=CC=CC=2N=N1.CN1CCOCC1.[NH2:53][CH:54]([C:57]1[CH:58]=[N:59][CH:60]=[CH:61][CH:62]=1)[CH2:55][OH:56]>CN(C=O)C.O>[F:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:2]([F:1])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([C:16]([NH:53][CH:54]([C:57]3[CH:58]=[N:59][CH:60]=[CH:61][CH:62]=3)[CH2:55][OH:56])=[O:17])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1

참가 물질

7

반응물 4

HCID 79724-MethylmorpholineHCID 27345901-(3-Pyridinyl)-2-hydroxyethylamineHCID 867178728-((2,6-Difluorobenzyl)oxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylic acidHCID 178484679HCID 178484679, 화합물

생성물 1

HCID 90115765rac-8-[(2,6-Difluorobenzyl)oxy]-N-[2-hydroxy-1-(pyridin-3-yl)ethyl]-2-methylimidazo[1,2-a]-pyridine-3-carboxamide

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

150 mg (0.47 mmol) of 8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid, 227 mg (0.71 mmol) of (benzotriazol-1-yloxy)bisdimethylaminomethylium fluoroborate (TBTU) and 238 mg (2.36 mmol) of 4-methylmorpholine were initially charged in 3 ml of DMF. After 10 min at RT, 98 mg (0.71 mmol) of 2-amino-2-(pyridin-3-yl)ethanol were added and the mixture was stirred at room temperature overnight. About 25 ml of water were added to the reaction solution and the precipitate formed was stirred for another 30 min, filtered off, washed thoroughly with water and dried under high vacuum overnight. The crude product was purified by silica gel chromatography (mobile phase: dichloromethane:methanol gradient). The product fractions were concentrated and stirred with acetonitrile. The solid obtained was filtered off and dried. This gave 40 mg of the target compound (20% of theory, purity 100%).

후처리

  1. customthe precipitate formed
  2. stirringwas stirred for another 30 min
  3. filtrationfiltered off
  4. washwashed thoroughly with water
  5. customdried under high vacuum overnight
  6. customThe crude product was purified by silica gel chromatography (mobile phase: dichloromethane:methanol gradient)
  7. concentrationThe product fractions were concentrated
  8. stirringstirred with acetonitrile
  9. customThe solid obtained
  10. filtrationwas filtered off
  11. customdried

출처 및 근거

ORD 기록
ord-e5cddc84e7974436b503583943fb76a6
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778964B2

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