Water → N-(benzo[d]thiazol-2-yl)-2-(4-chloro-5-formylthiazol-2-yl)-1,2,3,4-tetrahydroisoquinoline-8-carboxamide

HRID 1518313노트

반응식

HRID 1518313 반응식
Cl.Cl.[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[NH:12][C:13]([C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:24]=1[CH2:23][NH:22][CH2:21][CH2:20]2)=[O:14].Cl[C:26]1[S:27][C:28]([CH:32]=[O:33])=[C:29]([Cl:31])[N:30]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>CC(N(C)C)=O>[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[NH:12][C:13]([C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:24]=1[CH2:23][N:22]([C:26]1[S:27][C:28]([CH:32]=[O:33])=[C:29]([Cl:31])[N:30]=1)[CH2:21][CH2:20]2)=[O:14]

참가 물질

6

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 14886722,4-Dichloro-1,3-thiazole-5-carboxaldehydeHCID 86644320N-(benzo[d]thiazol-2-yl)-1,2,3,4-tetrahydroisoquinoline-8-carboxamide dihydrochloride

생성물 1

HCID 59447544N-(benzo[d]thiazol-2-yl)-2-(4-chloro-5-formylthiazol-2-yl)-1,2,3,4-tetrahydroisoquinoline-8-carboxamide수율 92.3%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

반응 조건

온도
60 °C

실험 절차

A mixture of compound 1B (3.82 g, 10 mmol), 2,4-dichlorothiazole-5-carbaldehyde (1.82 g, 10 mmol), and Cs2CO3 (9.77 g, 30 mmol) in DMA (30 mL) was heated at 60° C. for 8 hours, cooled to rt and then poured into water (500 mL). The solid was collected by filtration and dried in a vacuum oven overnight (60° C.) to provide 4.2 g of the desired product (45A): 1H NMR (DMSO-d6): δ 12.66 (s, 1H), 9.69 (s, 1H), 8.00 (d, J=7.82 Hz, 1H), 7.77 (d, J=8.06 Hz, 1H), 7.73 (d, J=7.58 Hz, 1H), 7.40-7.49 (m, 3H), 7.33-7.36 (m, 1H), 5.04 (s, 2H), 3.82 (t, J=5.92 Hz, 2H), 3.11 (t, J=6.16 Hz, 2H). MS (ESI(+)): m/z 455 (M+H).

후처리

  1. temperaturecooled to rt
  2. filtrationThe solid was collected by filtration
  3. customdried in a vacuum oven overnight (60° C.)

출처 및 근거

ORD 기록
ord-bf4f93b9f1524b199f663f6c10109e0f
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08232273B2

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