Potassium Carbonate → HCID 68576502、化合物

HRID 273038

反応式

HRID 273038 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][CH2:8][C:9]1([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.Br[CH2:23][CH2:24][CH2:25][CH2:26][Cl:27].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:27][CH2:26][CH2:25][CH2:24][CH2:23][O:21][C:18]1[CH:19]=[CH:20][C:15]([C:9]2([CH2:8][NH:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)=[CH:16][CH:17]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 813641-Bromo-4-chlorobutaneHCID 685779444-{4-[(pyridin-2-ylamino)methyl]tetrahydro-2H-pyran-4-yl}phenol

生成物 1

HCID 68576502HCID 68576502、化合物収率 63.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

4-{4-[(pyridin-2-ylamino)methyl]tetrahydro-2H-pyran-4-yl}phenol (220 mg, 0.775 mmol), 1-bromo-4-chlorobutane (146 mg, 0.852 mmol) and potassium carbonate (118 mg, 0.852 mmol) were stirred in DMF (1 ml) at 60° C. for 24 hours until complete. Reaction was partitioned between ethyl acetate (50 ml) and water (75 ml). The organic layer was separated and washed further with water (2×30 ml), then dried over sodium sulphate, filtered and concentrated in vacuo. The crude compound was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:ammonia (100:0:0 to 98:2:0.2 by volume) to give the title compound (184 mg, 63%) as a yellow solid. LRMS APCI+ m/z 375 [MH]+.

後処理

  1. customReaction
  2. customwas partitioned between ethyl acetate (50 ml) and water (75 ml)
  3. customThe organic layer was separated
  4. washwashed further with water (2×30 ml)
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude compound was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:ammonia (100:0:0 to 98:2:0.2 by volume)

出典と根拠

ORDレコード
ord-70f48d7f05ab4002b967c01107e0339e
出典データセット
uspto-grants-2008_11
特許番号
US07456164B2

関連ノート

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