Triethylamine → 2,3-Dimethyl-8-(2-(2-(benzyloxy)ethyl)-6-methylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxamide

HRID 427520ノート

反応式

HRID 427520 の反応式
S(O)(=O)(=O)C.[NH2:6][C:7]1[C:8]2[N:9]([C:16]([CH3:20])=[C:17]([CH3:19])[N:18]=2)[CH:10]=[C:11]([C:13]([NH2:15])=[O:14])[CH:12]=1.[CH2:21]([O:28][CH2:29][CH2:30][C:31]1[CH:38]=[CH:37][CH:36]=[C:35]([CH3:39])[C:32]=1[CH:33]=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C([BH3-])#N.[Na+].C(N(CC)CC)C>CO.[Cl-].[Zn+2].[Cl-]>[CH2:21]([O:28][CH2:29][CH2:30][C:31]1[CH:38]=[CH:37][CH:36]=[C:35]([CH3:39])[C:32]=1[CH2:33][NH:6][C:7]1[C:8]2[N:9]([C:16]([CH3:20])=[C:17]([CH3:19])[N:18]=2)[CH:10]=[C:11]([C:13]([NH2:15])=[O:14])[CH:12]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 183574358-Amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide mesylateHCID 183574522-[2-(Benzyloxy)ethyl]-6-methylbenzaldehyde

生成物 1

HCID 121489202,3-Dimethyl-8-(2-(2-(benzyloxy)ethyl)-6-methylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxamide収率 7.7%

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 887Methanol溶媒2 回

実験手順

To a solution of 8-Amino-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide mesylate 1.4 g (0.0038 mol) in methanol (20 ml) in a nitrogen atmosphere was added zinc chloride (1.0 g, 0.0039 mol) solved in methanol(10 ml) and the mixture was stirred for 30 min. To the mixture were added 2-[2-(benzyloxy)ethyl]-6-methylbenzaldehyde (1.0 g, 0.0039 mol) and sodium cyano borohydride (0.48 g, 0.0076 mol) and the mixture was refluxed overnight. The reation mixture was cooled to room temperature, triethylamine (4 ml) was added, the mixture was stirred for 30 min, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using methylene chloride:methanol (9:1) as eluent. The residue was solved in diethyl ether, treated with diethyl ether/HCl and the precipitated product as HCl salt was filtered off . The salt was soloved in methylene chloride and washed with saturated sodium carbonate. The organic layer was separated, washed with water, dried and evaporated under reduced pressure to give 0.13 g (7.7 g) of the title compound.

後処理

  1. temperaturethe mixture was refluxed overnight
  2. stirringthe mixture was stirred for 30 min
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel
  5. additiontreated with diethyl ether/HCl
  6. filtrationthe precipitated product as HCl salt was filtered off
  7. washwashed with saturated sodium carbonate
  8. customThe organic layer was separated
  9. washwashed with water
  10. customdried
  11. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-f53561ec9cae492e8b261122fc119cf6
出典データセット
uspto-grants-2001_11
特許番号
US06313137B1

反応ノート

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