Hydrochloric Acid → 6,6-dimethyl-morpholine-3-carboxylic acid (6-chloro-9H-beta-carbolin-8-yl)-amide

HRID 552232노트

반응식

HRID 552232 반응식
C(OC([N:8]1[CH:13]([C:14](=[O:30])[NH:15][C:16]2[CH:17]=[C:18]([Cl:29])[CH:19]=[C:20]3[C:28]=2[NH:27][C:26]2[CH:25]=[N:24][CH:23]=[CH:22][C:21]3=2)[CH2:12][O:11][C:10]([CH3:32])([CH3:31])[CH2:9]1)=O)(C)(C)C.Cl.CCOCC>CO.O1CCOCC1>[Cl:29][C:18]1[CH:19]=[C:20]2[C:28](=[C:16]([NH:15][C:14]([CH:13]3[CH2:12][O:11][C:10]([CH3:32])([CH3:31])[CH2:9][NH:8]3)=[O:30])[CH:17]=1)[NH:27][C:26]1[CH:25]=[N:24][CH:23]=[CH:22][C:21]2=1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 671644975-(6-chloro-9H-beta-carbolin-8-ylcarbamoyl)-2,2-dimethyl-morpholine-4-carboxylic acid tert-butyl ester

생성물 1

HCID 671642096,6-dimethyl-morpholine-3-carboxylic acid (6-chloro-9H-beta-carbolin-8-yl)-amide수율 119.2%

시약·촉매·용매 2

HCID 887Methanol용매HCID 312751,4-Dioxane용매

실험 절차

To a clear brown solution of 5-(6-chloro-9H-β-carbolin-8-ylcarbamoyl)-2,2-dimethyl-morpholine-4-carboxylic acid tert-butyl ester (10.4 g, 22.7 mmol) in methanol (41 mL) was added HCl in dioxane (4M, 91 mL). The reaction was stirred for 30 minutes at room temperature, during which time a pale brown precipitate began to form. The mixture was poured into a 250-mL volume of vigorously stirring Et2O. The resulting slurry was stirred at room temperature for 15 minutes, then filtered to yield a pale orange solid. The solid was placed on the high-vacuum pump overnight, after which 9.71 g of 6,6-dimethyl-morpholine-3-carboxylic acid (6-chloro-9H-β-carbolin-8-yl)-amide was obtained (99% yield). 1H-NMR (DMSO-d6, 300 MHz) δ 13.47 (s, 1); 11.77 (s, 1); 9.42 (s, 1); 8.86 (d, 1); 8.66 (d, 1); 8.58 (d, 1); 8.25 (d, 1); 4.41-4.37 (m, 2); 4.05 (dd, 1); 3.32-3.28 (m, 1); 3.04-3.00 (m, 1); 1.34 (s, 3); 1.30 (s, 3). NH4OAc standard conditions. DAD Rf=1.48 min. M+H=359.

후처리

  1. customto form
  2. stirringThe resulting slurry was stirred at room temperature for 15 minutes
  3. filtrationfiltered
  4. customto yield a pale orange solid
  5. customwas placed on the high-vacuum pump overnight

출처 및 근거

ORD 기록
ord-2392f4ab8d3f4b8a9042c8e304a49636
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07951801B2

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