Dichloromethane → {6-[2-(4-Amino-6-methoxy-[1,5]naphthyridin-3-yloxy)-acetyl]-pyridin-3-yl}-carbamic acid tert-butyl ester

HRID 2273213ノート

反応式

HRID 2273213 の反応式
C(=O)([O-])[O-].[K+].[K+].[C:7]([O:11][C:12](=[O:24])[NH:13][C:14]1[CH:15]=[N:16][C:17]([C:20](=[O:23])[CH2:21]Br)=[CH:18][CH:19]=1)([CH3:10])([CH3:9])[CH3:8].[NH2:25][C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[C:33]([O:36][CH3:37])[N:34]=2)[N:29]=[CH:28][C:27]=1[OH:38].ClCCl>CN(C)C=O.CO>[C:7]([O:11][C:12](=[O:24])[NH:13][C:14]1[CH:15]=[N:16][C:17]([C:20](=[O:23])[CH2:21][O:38][C:27]2[CH:28]=[N:29][C:30]3[C:35]([C:26]=2[NH2:25])=[N:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=3)=[CH:18][CH:19]=1)([CH3:10])([CH3:9])[CH3:8]

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 86671533tert-butyl N-[6-(2-bromoacetyl)pyridin-3-yl]carbamateHCID 1363447124-Amino-6-methoxy-[1,5]naphthyridin-3-ol

生成物 1

HCID 67248964{6-[2-(4-Amino-6-methoxy-[1,5]naphthyridin-3-yloxy)-acetyl]-pyridin-3-yl}-carbamic acid tert-butyl ester収率 30.7%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

実験手順

Potassium carbonate (140 mg, 1.02 mmol, 1.5 eq) is added at room temperature to a stirred solution of [6-(2-bromo-acetyl)-pyridin-3-yl]-carbamic acid tert-butyl ester (220 mg, 0.70 mmol, 1.0 eq) and 4-amino-6-methoxy-[1,5]naphthyridin-3-ol (130 mg, 0.69 mmol, 1.0 eq) in N,N-dimethylformamide (10 mL). After 30 minutes stirring at room temperature, solvent is removed and the residue is extracted with ethyl acetate (3×15 mL) and water (10 mL). The combined organic layers are washed with brine, dried over sodium sulfate, filtered and concentrated to give the crude product that is purified by column chromatography (silica gel, eluent: dichloromethane:methanol, 100:1, v/v) to afford {6-[2-(4-amino-6-methoxy-[1,5]naphthyridin-3-yloxy)-acetyl]-pyridin-3-yl}-carbamic acid tert-butyl ester as a red-brown solid (90 mg, 24% yield).

後処理

  1. customsolvent is removed
  2. extractionthe residue is extracted with ethyl acetate (3×15 mL) and water (10 mL)
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude product that
  8. customis purified by column chromatography (silica gel, eluent

出典と根拠

ORDレコード
ord-75d3505db01547f0a81979a7691de369
出典データセット
uspto-grants-2015_09
特許番号
US09120822B2

反応ノート

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