Dimethyl Sulfoxide → Benzo[1,3]dioxol-5-ylmethyl-{3-[(3-chloro-[1,2,4]thiadiazol-5-yl)-methyl-amino]-propyl}-carbamic acid tert-butyl ester

HRID 1170467노트

반응식

HRID 1170467 반응식
[C:1]([O:5][C:6](=[O:23])[N:7]([CH2:13][C:14]1[CH:22]=[CH:21][C:17]2[O:18][CH2:19][O:20][C:16]=2[CH:15]=1)[CH2:8][CH2:9][CH2:10][NH:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].[Cl:24][C:25]1[N:29]=[C:28](Cl)[S:27][N:26]=1.CS(C)=O>O>[C:1]([O:5][C:6](=[O:23])[N:7]([CH2:13][C:14]1[CH:22]=[CH:21][C:17]2[O:18][CH2:19][O:20][C:16]=2[CH:15]=1)[CH2:8][CH2:9][CH2:10][N:11]([C:28]1[S:27][N:26]=[C:25]([Cl:24])[N:29]=1)[CH3:12])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 679Dimethyl SulfoxideHCID 2725055Dichloro-1,2,4-thiadiazoleHCID 46899438Benzo[1,3]dioxol-5-ylmethyl-(3-methylamino-propyl)-carbamic acid tert-butyl ester

생성물 1

HCID 46899439Benzo[1,3]dioxol-5-ylmethyl-{3-[(3-chloro-[1,2,4]thiadiazol-5-yl)-methyl-amino]-propyl}-carbamic acid tert-butyl ester수율 69%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A solution of benzo[1,3]dioxol-5-ylmethyl-(3-methylamino-propyl)-carbamic acid tert-butyl ester (10 g, 46 mmol), 3,5-dichloro-1,2,4-thiadiazole (7.1 g, 46 mmol), DMSO (20 mL) and TEA (20 mL) was stirred at r.t. for 20 min. Water (150 mL) was added and the solution was extracted with ethyl acetate (2×150 mL), washed with brine and dried over Na2SO4. Evaporation of the solvent gave 14 g (69%) of benzo[1,3]dioxol-5-ylmethyl-{3-[(3-chloro-[1,2,4]thiadiazol-5-yl)-methyl-amino]-propyl}-carbamic acid tert-butyl ester as a clear gum. The product was used directly in the next step. 1H-NMR (400 MHz, CD3OD) δ 6.77 (m, 3H), 5.96 (s, 2H), 4.35 (s, 2H), 3.4-3.0 (m, 6H), 1.84 (br s, 3H), 1.50 (s, 9H).

후처리

  1. extractionthe solution was extracted with ethyl acetate (2×150 mL)
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. customEvaporation of the solvent

출처 및 근거

ORD 기록
ord-a935dc9618684b71b012c17eeb1e8cf2
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07825256B2

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