Acetic Acid → 1,1-Dimethylethyl N-(5-bromo-1,2-dihydro-1-methyl-2-oxo-3-pyridinyl)-N-[5-[(ethylamino)methyl]-2-pyridinyl]carbamate

HRID 2069732ノート

反応式

HRID 2069732 の反応式
[C:1]([O:5][C:6](=[O:25])[N:7]([C:16]1[C:17](=[O:24])[N:18]([CH3:23])[CH:19]=[C:20]([Br:22])[CH:21]=1)[C:8]1[CH:13]=[CH:12][C:11]([CH:14]=O)=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:26]([NH2:28])[CH3:27].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C1COCC1.C(Cl)Cl>[C:1]([O:5][C:6](=[O:25])[N:7]([C:16]1[C:17](=[O:24])[N:18]([CH3:23])[CH:19]=[C:20]([Br:22])[CH:21]=1)[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][NH:28][CH2:26][CH3:27])=[CH:10][N:9]=1)([CH3:3])([CH3:4])[CH3:2]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 6341Ethylamine2 回HCID 5049666Sodium triacetoxyborohydrideHCID 59473778HCID 59473778、化合物

生成物 1

HCID 594737951,1-Dimethylethyl N-(5-bromo-1,2-dihydro-1-methyl-2-oxo-3-pyridinyl)-N-[5-[(ethylamino)methyl]-2-pyridinyl]carbamate収率 63.5%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

(5-bromo-1-methyl-2-oxo-1,2-dihydro-pyridin-3-yl)-(5-formyl-pyridin-2-yl)-carbamic acid tert-butyl ester (500 mg, 1.22 mmol), ethanamine (6.12 ml of a 2.0 M solution in THF), sodium triacetoxyborohydride (649 mg, 3.06 mmol), and acetic acid (147 mg, 2.45 mmol) were added to a 20 ml microwave vial. The vial was capped and heated in a sand bath at 40 degrees centigrade overnight. TLC and LCMS analysis showed the reaction to be incomplete. Another 6 ml of ethanamine was added to the vial and the reaction was heated again at 40 degrees centigrade overnight. The reaction was diluted with DCM and washed with saturated aqueous sodium bicarbonate, dried and concentrated. The crude product was purified by flash chromatography using 10% methanol in DCM to give 340 mg (63.5%) of (5-bromo-1-methyl-2-oxo-1,2-dihydro-pyridin-3-yl)-(5-ethylaminomethyl-pyridin-2-yl)-carbamic acid tert-butyl ester.

後処理

  1. customThe vial was capped
  2. temperatureheated in a sand bath at 40 degrees centigrade overnight
  3. customthe reaction
  4. temperaturewas heated again at 40 degrees centigrade overnight
  5. washwashed with saturated aqueous sodium bicarbonate
  6. customdried
  7. concentrationconcentrated
  8. customThe crude product was purified by flash chromatography

出典と根拠

ORDレコード
ord-c8c9b80daec24229afadd48048f85cdb
出典データセット
uspto-grants-2012_10
特許番号
US08299077B2

反応ノート

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