Diisopropylethylamine → HCID 57725478、化合物

HRID 2370558ノート

反応式

HRID 2370558 の反応式
[Br:1][C:2]1[C:10]2[S:9][C:8](Cl)=[N:7][C:6]=2[CH:5]=[CH:4][C:3]=1[O:12][CH3:13].Cl.[NH2:15][C@@H:16]1[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]1[OH:22].CCN(C(C)C)C(C)C>CN1C(=O)CCC1.C(=O)(O)[O-].[Na+]>[Br:1][C:2]1[C:10]2[S:9][C:8]([NH:15][C@@H:16]3[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]3[OH:22])=[N:7][C:6]=2[CH:5]=[CH:4][C:3]=1[O:12][CH3:13]

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 12228412Cyclohexanol, 2-amino-, hydrochloride (1:1), (1R,2R)-HCID 23148836HCID 23148836、化合物

生成物 1

HCID 57725478HCID 57725478、化合物

試薬・触媒・溶媒 2

HCID 13387N-methyl-2-pyrrolidone溶媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
125 °C

実験手順

To the solution of 7-bromo-2-chloro-6-methoxybenzo[d]thiazole (150 mg, 0.539 mmol, 1.0 eq) in 1 mL of NMP was added (1R,2R)-2-aminocyclohexanol hydrochloride (0.123 mg, 0.809 mmol, 1.5 eq) and DIPEA (263 μL, 1.503 mmol, 2.8 eq) at room temperature. The reaction mixture was stirred at 125° C. for 12 hours, thereafter the mixture was diluted with saturated sodium bicarbonate solution (ca. 100 mL) and aqueous layer extracted with ethyl acetate (ca. 200 mL×3). Combined organic layers were dried over sodium sulfate, filtered and condensed under reduced pressure to give crude product as brown oil which was sufficiently pure and was carried to next step without further purification. LC/MS (m/z) [359.0] (MH+)

後処理

  1. extractionextracted with ethyl acetate (ca. 200 mL×3)
  2. dry with materialCombined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. customcondensed under reduced pressure
  5. customto give crude product as brown oil which
  6. customwas carried to next step without further purification

出典と根拠

ORDレコード
ord-bfd8d07ec73a4883b9663cf764d875ac
出典データセット
uspto-grants-2014_04
特許番号
US08710048B2

反応ノート

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