1,1,1-Trimethoxybutane → tert-butyl 4-[(7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]piperidine-1-carboxylate

HRID 1818193

反応式

HRID 1818193 の反応式
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1)=[CH:9][CH:8]=[C:7]([Br:27])[CH:6]=2.[C:28](OC)(OC)(OC)[CH2:29][CH2:30][CH3:31]>>[Br:27][C:7]1[CH:8]=[CH:9][C:10]2[C:11]3[N:12]([CH2:13][CH:14]4[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:24])([CH3:26])[CH3:25])=[O:21])[CH2:16][CH2:15]4)[C:28]([CH2:29][CH2:30][CH3:31])=[N:1][C:2]=3[CH:3]=[N:4][C:5]=2[CH:6]=1

参加物

3

反応物 2

HCID 1235121,1,1-TrimethoxybutaneHCID 21984428Tert-butyl 4-[(3-amino-7-bromoquinolin-4-ylamino)methyl]piperidine-1-carboxylate

生成物 1

HCID 21984032tert-butyl 4-[(7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]piperidine-1-carboxylate収率 77.9%

実験手順

The method described in Part A of Examples 142-144 was used to treat tert-butyl 4-[(3-amino-7-bromoquinolin-4-ylamino)methyl]piperidine-1-carboxylate (15.0 g, 34.5 mmol) with trimethyl orthobutyrate (5.62 g, 37.9 mmol). After completion, the reaction mixture was concentrated under reduced pressure, and the residue was purified by flash column chromatography on silica gel (eluting with 95:5 chloroform:CMA) followed by recrystallization from ethyl acetate to provide 13.1 g of tert-butyl 4-[(7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]piperidine-1-carboxylate as a white solid, mp 215-216° C.

後処理

  1. concentrationAfter completion, the reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by flash column chromatography on silica gel (eluting with 95:5 chloroform:CMA)
  3. customfollowed by recrystallization from ethyl acetate

出典と根拠

ORDレコード
ord-f532e941020444f0a90e5545750eff9b
出典データセット
uspto-grants-2009_10
特許番号
US07598382B2

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