Ammonia → N,N-diisobutyl-1-{3-[methyl(2-pyridin-2-ylethyl)amino]propyl}-2-[(3,4,5-trimethoxyphenyl)amino]-1H-benzimidazole-5-carboxamide hydrochloride

HRID 883682

반응식

HRID 883682 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:13]=[C:14]=S)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[NH2:16][C:17]1[CH:18]=[C:19]([CH:31]=[CH:32][C:33]=1[NH:34][CH2:35][CH2:36][CH2:37][N:38]([CH3:47])[CH2:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][N:42]=1)[C:20]([N:22]([CH2:27][CH:28]([CH3:30])[CH3:29])[CH2:23][CH:24]([CH3:26])[CH3:25])=[O:21].N.[ClH:49]>O1CCCC1.C(OCC)C>[ClH:49].[CH2:27]([N:22]([CH2:23][CH:24]([CH3:26])[CH3:25])[C:20]([C:19]1[CH:31]=[CH:32][C:33]2[N:34]([CH2:35][CH2:36][CH2:37][N:38]([CH3:47])[CH2:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][N:42]=3)[C:14]([NH:13][C:5]3[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=3)=[N:16][C:17]=2[CH:18]=1)=[O:21])[CH:28]([CH3:29])[CH3:30]

참가 물질

7

반응물 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 1189003,4,5-Trimethoxyphenyl isothiocyanateHCID 69026788HCID 69026788, 화합물

생성물 1

HCID 69029004N,N-diisobutyl-1-{3-[methyl(2-pyridin-2-ylethyl)amino]propyl}-2-[(3,4,5-trimethoxyphenyl)amino]-1H-benzimidazole-5-carboxamide hydrochloride

시약·촉매·용매 2

HCID 3283Diethyl Ether용매2회HCID 8028Tetrahydrofuran용매

실험 절차

3,4,5 trimethoxyphenylisothiocyanate (27 mg, 1.2 eq) and N-methylcyclohexylcarbodiimide-N-methyl-polystyrene resin (acquired from Novabiochem; load 1.69 mmol/g, 236 mg, 4 eq) are added successively to a solution of 3-amino-N,N-diisobutyl-4-({3-[methyl(2-pyridin-2-ylethyl)amino]propyl}amino) benzamide (48 mg, 1 eq) in tetrahydrofuran (2 ml). The mixture is heated under reflux for 18 hours then cooled down to ambient temperature and aminomethyl polystyrene resin (acquired from Novabiochem, 2 eq) is added. After stirring for 4 hours at ambient temperature, the mixture is filtered on frit and the filtrate is concentrated under reduced pressure at 40° C. The residue obtained is dissolved in ethyl ether and a solution of 1N HCl in ethyl ether is added dropwise in order to produce the expected compound in the form of the hydrochloride salt (80 mg, 89% yield).

후처리

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 18 hours
  3. filtrationthe mixture is filtered on frit
  4. concentrationthe filtrate is concentrated under reduced pressure at 40° C
  5. customThe residue obtained

출처 및 근거

ORD 기록
ord-eb0683ce06824d11a52c7523cf43050e
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08236965B2

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