Acetyl chloride → (2S,4S)-4-(8-chloro-2-(4-isopropylthiazol-2-yl)-7-methoxyquinolin-4-yloxy)-N-(hex-5-enyl)-N-methylpyrrolidine-2-carboxamide hydrochloride

HRID 1675451노트

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HRID 1675451 반응식
[Cl:1][C:2]1[C:3]([O:43][CH3:44])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[S:13][CH:14]=[C:15]([CH:17]([CH3:19])[CH3:18])[N:16]=1)[CH:8]=[C:7]2[O:20][C@@H:21]1[CH2:25][N:24](C(OC(C)(C)C)=O)[C@H:23]([C:33](=[O:42])[N:34]([CH2:36][CH2:37][CH2:38][CH2:39][CH:40]=[CH2:41])[CH3:35])[CH2:22]1.C(Cl)(=O)C>CO>[ClH:1].[Cl:1][C:2]1[C:3]([O:43][CH3:44])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[S:13][CH:14]=[C:15]([CH:17]([CH3:19])[CH3:18])[N:16]=1)[CH:8]=[C:7]2[O:20][C@@H:21]1[CH2:25][NH:24][C@H:23]([C:33]([N:34]([CH2:36][CH2:37][CH2:38][CH2:39][CH:40]=[CH2:41])[CH3:35])=[O:42])[CH2:22]1

참가 물질

4

반응물 2

HCID 6367Acetyl chlorideHCID 66650750(2S,4S)-tert-butyl 4-(8-chloro-2-(4-isopropylthiazol-2-yl)-7-methoxyquinolin-4-yloxy)-2-(hex-5-enyl(methyl)carbamoyl)pyrrolidine-1-carboxylate2회

생성물 1

HCID 66650405(2S,4S)-4-(8-chloro-2-(4-isopropylthiazol-2-yl)-7-methoxyquinolin-4-yloxy)-N-(hex-5-enyl)-N-methylpyrrolidine-2-carboxamide hydrochloride

시약·촉매·용매 1

HCID 887Methanol용매2회

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온도
40 °C

실험 절차

Compound 134 (20.37 g) was suspended in anhydrous methanol (120 mL) under argon at room temperature. Separately acetyl chloride (3 eq.) was added to anhydrous methanol (70 mL) at 10-20° C. This solution was added to the compound 134 solution at 5° C. The reaction mixture was heated at 40° C. for 3-4 hrs. After the completion of the reaction, the reaction mixture was concentrated under vacuum and then co-evaporated with 100 mL of anhydrous dichloromethane. The product was then dried in a vacuum oven at 40-45° C. Compound 135 (19.81 g) was recovered as a yellow foam in quantitative yield and 100% purity (HPLC).

후처리

  1. customAfter the completion of the reaction
  2. concentrationthe reaction mixture was concentrated under vacuum
  3. customThe product was then dried in a vacuum oven at 40-45° C
  4. customCompound 135 (19.81 g) was recovered as a yellow foam in quantitative yield and 100% purity (HPLC)

출처 및 근거

ORD 기록
ord-80d0c96ed0bc4b5ebf3b47622f4a9c60
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08003659B2

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