Hydrochloric Acid → 1-(4,5-dihydro-1H-imidazol-2-ylmethyl)-3-methanesulfonyl-6-methyl-1H-indole

HRID 23381

반응식

HRID 23381 반응식
[CH3:1][S:2]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([CH3:14])=[CH:11][CH:12]=2)[N:7]([CH2:15][C:16]#[N:17])[CH:6]=1)(=[O:4])=[O:3].CC1C=C2C([CH:23]=[CH:24][NH:25]2)=CC=1.C(N)CN.Cl>CO.C(O)C.O.C(=S)=S>[NH:17]1[CH2:23][CH2:24][N:25]=[C:16]1[CH2:15][N:7]1[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([CH3:14])[CH:9]=2)[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6]1

참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 3301EthylenediamineHCID 1379281H-Indole, 6-methyl-HCID 22574083(3-Methanesulfonyl-6-methyl-indol-1-yl)-acetonitrile

생성물 1

HCID 129974411-(4,5-dihydro-1H-imidazol-2-ylmethyl)-3-methanesulfonyl-6-methyl-1H-indole

시약·촉매·용매 4

HCID 702Ethanol용매HCID 887Methanol용매HCID 962Water용매HCID 6348Carbon Disulfide용매

반응 조건

온도
142 °C

실험 절차

(3-Methanesulfonyl-6-methyl-indol-1-yl)-acetonitrile (0.4 g, 1.611 mmole) prepared from 6-methylindole as described in Steps 1-4 above, was added to ethylene diamine (4.3 ml, 438 mmole) in a reaction tube. A single drop of carbon disulfide was carefully added. The mixture was heated in a microwave reactor at 142° C. for 30 minutes. Upon cooling, the reaction mixture was poured into a mixture of ice and water, stirred 20 minutes and filtered. The colorless precipitate collected was washed with water (20 ml) and dried under vacuum at room temperature. The free base thus obtained (420 mg, 90% yield) was converted into the hydrochloride salt by first dissolving in methanol and then adding an excess of HCl in ethanol. The mixture was stripped to dryness and recrystallized from a mixture of ethyl acetate-methanol to afford 344 mg of 1-(4,5-dihydro-1H-imidazol-2-ylmethyl)-3-methanesulfonyl-6-methyl-1H-indole, mp >300° C. as the hydrochloride salt.

후처리

  1. temperatureUpon cooling
  2. filtrationfiltered
  3. customThe colorless precipitate collected
  4. washwas washed with water (20 ml)
  5. customdried under vacuum at room temperature
  6. customThe free base thus obtained (420 mg, 90% yield)
  7. customrecrystallized from a mixture of ethyl acetate-methanol

출처 및 근거

ORD 기록
ord-f263b8a22ad24836ac45316e00c6321c
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06852726B2

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