Potassium Carbonate → HCID 57725678、化合物

HRID 1988475ノート

反応式

HRID 1988475 の反応式
[F:1][C:2]1[C:3]([O:12][CH3:13])=[CH:4][C:5]2[S:9][C:8]([NH2:10])=[N:7][C:6]=2[CH:11]=1.Br[CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+]>CN1C(=O)CCC1>[CH:16]1([CH2:15][NH:10][C:8]2[S:9][C:5]3[CH:4]=[C:3]([O:12][CH3:13])[C:2]([F:1])=[CH:11][C:6]=3[N:7]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 137636Cyclohexane, (bromomethyl)-HCID 45076940HCID 45076940、化合物

生成物 1

HCID 57725678HCID 57725678、化合物収率 60%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
80 °C

実験手順

To the solution of 5-fluoro-6-methoxybenzo[d]thiazol-2-amine (350 mg, 1.76 mmol, 1.0 eq) in 2 mL of NMP was added bromomethyl cyclohexane (370 μL, 2.65 mmol, 1.5 eq) and potassium carbonate (366 mg, 2.65 mmol, 1.5 eq) at room temperature. The reaction mixture was stirred at 80° C. for 24 hours with subsequent addition of reagents till reaction completion and thereafter quenched with saturated sodium bicarbonate solution (100 mL) which was then extracted with ethyl acetate (125 mL×3), combined organic layers dried over sodium sulfate, filtered and condensed under reduced pressure. Purification of the crude over ISCO using slow gradient of 0%-50% ethyl acetate-hexane gave 310 mg of product in 60% yield. LC/MS (m/z) [295.1] (MH+)

後処理

  1. customquenched with saturated sodium bicarbonate solution (100 mL) which
  2. extractionwas then extracted with ethyl acetate (125 mL×3)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customcondensed under reduced pressure
  6. customPurification of the crude over ISCO

出典と根拠

ORDレコード
ord-a9c1a10d81f14159bc6f358d2a1a030d
出典データセット
uspto-grants-2009_06
特許番号
US07553854B2

反応ノート

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