5-Chloro-o-anisic acid → 5-chloro-N-(5-chlorothiazol-2-yl)-2-methoxybenzamide

HRID 78486

반응식

HRID 78486 반응식
Cl.[Cl:2][C:3]1[S:7][C:6]([NH2:8])=[N:5][CH:4]=1.[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([O:19][CH3:20])=[C:14]([CH:18]=1)[C:15](O)=[O:16].Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([O:19][CH3:20])=[C:14]([CH:18]=1)[C:15]([NH:8][C:6]1[S:7][C:3]([Cl:2])=[CH:4][N:5]=1)=[O:16]

참가 물질

7

반응물 4

HCID 769705-Chloro-o-anisic acidHCID 1487432-Amino-5-chlorothiazole hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

생성물 1

HCID 866189125-chloro-N-(5-chlorothiazol-2-yl)-2-methoxybenzamide

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine용매

실험 절차

A mixture of 5-chlorothiazol-2-amine hydrochloride (513 mg, 3 mmol), 5-chloro-2-methoxybenzoic acid (670 mg, 3.6 mmol), 1-ethyl-3-[3-(dimethylamino)propyl]-carbodiimide hydrochloride (1.15 g, 6 mmol), 1-hydroxybenzotriazole hydrate (810 mg, 6 mmol) and 4-(dimethylamino)pyridine (73 mg, 0.6 mmol) in pyridine was stirred at room temperature for 2 hours. The volatiles were removed under vacuum, and the resulting mixture was diluted with water and extracted with ethyl acetate. The organic extract was dried (Na2SO4), filtered and concentrated. The residue was washed with a small amount of ethyl acetate, and filtered to afford the title compound. MS (ESI) m/z 303 (M+H)+.

후처리

  1. customThe volatiles were removed under vacuum
  2. additionthe resulting mixture was diluted with water
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. dry with materialwas dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. washThe residue was washed with a small amount of ethyl acetate
  9. filtrationfiltered

출처 및 근거

ORD 기록
ord-3697807c9d7c4d5d9ac0188335d27475
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841334B2

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