Hydrochloric Acid → HCID 67466031、化合物

HRID 540362ノート

反応式

HRID 540362 の反応式
[O:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=O)[CH2:3][CH2:2]1.[Br:10][C:11]1[CH:20]=[C:19]2[C:14]([CH2:15][CH2:16][N:17](C=O)[CH2:18]2)=[CH:13][CH:12]=1.[B-](F)(F)(F)F.CN(C(ON1C(=O)C=CC=C1)=[N+](C)C)C.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)C(C)C)C.Cl>C(Cl)Cl.CCOCC>[Br:10][C:11]1[CH:20]=[C:19]2[C:14]([CH2:15][CH2:16][N:17]([C:7]([CH:4]3[CH2:3][CH2:2][O:1][CH2:6][CH2:5]3)=[O:9])[CH2:18]2)=[CH:13][CH:12]=1

参加物

9

反応物 6

HCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 219302Oxane-4-carboxylic acidHCID 2733204O-(2-Oxo-1(2H)-pyridyl)-N,N,N',N'-tetramethyluronium TetrafluoroborateHCID 735546127-Bromo-3,4-dihydroisoquinoline-2(1H)-carbaldehyde

生成物 1

HCID 67466031HCID 67466031、化合物収率 108%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒2 回HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of tetrahydropyran-4-carboxylic acid 130 mg (1 mmol) in DCM (5 mL) was added 7-bromo-3,4-dihydro-1H-isoquinoline-2-carbaldehyde (200 mg, 1 mmol), followed by TPTU (326 mg) and HOBt (148 mg). The solution was cooled to ice-water bath. To this solution was added ethyl diisopropylamine (0.4 mL). The yellow solution was allowed to stir under nitrogen overnight. LC/MS showed the reaction was complete. The reaction was quenched by addition of sodium bicarbonate solution (5 mL) and DCM (30 mL). The two layers were separated, and the aqueous layer was extracted with DCM (20 mL×2). The combined DCM extracts were washed with sodium bicarbonate (20 mL), and brine (15 mL×2), dried (anhydrous potassium carbonate), filtered, and concentrated in vacuo. The crude product was purified on a silica gel column, eluted with 5-10% MeOH in DCM to get a yellow semi-solid. This was taken in DCM and ether (5 mL) and treated with 0.5 mL of 1N HCl in ether. The white powder was collected and dried to get 0.35 g (100% yield) of the titled compound as a yellow solid.

後処理

  1. temperatureThe solution was cooled to ice-water bath
  2. customThe reaction was quenched by addition of sodium bicarbonate solution (5 mL) and DCM (30 mL)
  3. customThe two layers were separated
  4. extractionthe aqueous layer was extracted with DCM (20 mL×2)
  5. washThe combined DCM extracts were washed with sodium bicarbonate (20 mL), and brine (15 mL×2)
  6. dry with materialdried (anhydrous potassium carbonate)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified on a silica gel column
  10. washeluted with 5-10% MeOH in DCM
  11. customto get a yellow semi-solid
  12. customThe white powder was collected
  13. customdried

出典と根拠

ORDレコード
ord-ad50b77f45414ba893b7f74afb7fac82
出典データセット
uspto-grants-2014_10
特許番号
US08871788B2

反応ノート

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