Diisopropylethylamine → HCID 57725706、化合物

HRID 2067181ノート

反応式

HRID 2067181 の反応式
Cl[C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.Cl.[NH2:14][C@@H:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C@H:16]1[OH:21].CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[CH3:12][O:11][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([NH:14][C@@H:15]3[CH2:20][CH2:19][CH2:18][CH2:17][C@H:16]3[OH:21])[S:3][C:4]=2[CH:10]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 2731322-Chloro-6-methoxybenzothiazoleHCID 12228412Cyclohexanol, 2-amino-, hydrochloride (1:1), (1R,2R)-

生成物 1

HCID 57725706HCID 57725706、化合物収率 76.2%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
115 °C

実験手順

To a solution of 2-chloro-6-methoxybenzo[d]thiazole (1.0 g, 5 mmol) in 5.5 mL of NMP was added (1R,2R)-2-aminocyclohexanol hydrochloride (910 mg, 6 mmol) and DIPEA (2.44 mL, 14 mmol). The reaction solution was stirred at 115° C. for 96 hours. The crude reaction solution was purified by preparative HPLC to give purified fractions that was combined and neutralized with solid NaHCO3. The resulting solution was extracted with EtOAc (2×300 mL). The combined organic layers were washed with water (60 mL) and brine (60 mL), then dried over Na2SO4 and evaporated in vacuo to give (1R,2R)-2-(6-methoxybenzo[d]thiazol-2-ylamino)cyclohexanol (1.06 g, 3.81 mmol) as an ivory solid. ES/MS m/z 279.1 (MH+).

後処理

  1. customThe crude reaction solution
  2. customwas purified by preparative HPLC
  3. customto give
  4. custompurified fractions that
  5. extractionThe resulting solution was extracted with EtOAc (2×300 mL)
  6. washThe combined organic layers were washed with water (60 mL) and brine (60 mL)
  7. dry with materialdried over Na2SO4
  8. customevaporated in vacuo

出典と根拠

ORDレコード
ord-3cf5d74336ad44d1a5e9a1171f80d1e2
出典データセット
uspto-grants-2012_10
特許番号
US08293769B2

反応ノート

読み込み中…