Methylamine → (2-[1-(6-Chloroimidazo[2,1-b]thiazole-5-sulfonyl)-1H-indol-3-yl]ethyl}methyl amine

HRID 1793858노트

반응식

HRID 1793858 반응식
Br[CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([S:13]([C:16]2[N:23]3[C:19]([S:20][CH:21]=[CH:22]3)=[N:18][C:17]=2[Cl:24])(=[O:15])=[O:14])[CH:5]=1.[CH3:25][NH2:26]>C1COCC1>[Cl:24][C:17]1[N:18]=[C:19]2[N:23]([C:16]=1[S:13]([N:6]1[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:4]([CH2:3][CH2:2][NH:26][CH3:25])=[CH:5]1)(=[O:14])=[O:15])[CH:22]=[CH:21][S:20]2

참가 물질

4

반응물 2

HCID 6329MethylamineHCID 112593493-(2-Bromoethyl)-1-(6-chloroimidazo[2,1-b]thiazole-5-sulfonyl)indole

생성물 1

HCID 10287437(2-[1-(6-Chloroimidazo[2,1-b]thiazole-5-sulfonyl)-1H-indol-3-yl]ethyl}methyl amine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
50 °C

실험 절차

A solution of 3-(2-bromoethyl)-1-(6-chloroimidazo[2,1-b]thiazole-5-sulfonyl) indole (92 mg, 0.20 mmol) in THF is treated with methyl amine (2M in methanol, 0.4 mL, 2 eq.), heated at 50° C. for 24 h, cooled and concentrated in vacuo. The resultant residue is purified by HPLC1 to give the title product as a white solid, 18.5 mg, identified by HPLC2 and mass spectral analyses. 1HPLC conditions (preparative): Gilson Preparative HPLC system; YMC Pro C18, 20 mm×50 mm ID, 5 uM column; 2 mL injection; Solvent A: 0.02% TFA/water; Solvent B: 0.02% TFA/acetonitrile; Gradient: Time 0: 95% A; 2 min: 95% A; 14 min: 10% A, 15 min: 10% A, 16 min: 95% A; Flow rate 22.5 mL/min; Detection: 254 nm DAD.2HPLC conditions (analytical): Hewlett Packard 1100 HPLC system; Waters Xterra C18, 2 mm×30 mm ID, 3 uM column; 5 uL injection; Solvent A: 0.02% TFA/water; Solvent B: 0.02% TFA/acetonitrile; Gradient: Time 0: 95% A; 0.2 min: 95% A; 3 min: 5% A; Flow rate 1.2 mL/min; Detection: 254 nm DAD.

후처리

  1. temperaturecooled
  2. concentrationconcentrated in vacuo
  3. customThe resultant residue is purified by HPLC1

출처 및 근거

ORD 기록
ord-6bd52bc0b8c04b8dbb5c45adfc8df241
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07022701B2

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