Ammonia → 5-[(diisobutylamino)methyl]-1-(3-{methyl[2-(2-pyridinyl)ethyl]amino}propyl)-N-(3,4,5-trimethoxyphenyl)-1H-benzimidazol-2-amine

HRID 1727424

反応式

HRID 1727424 の反応式
[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].[CH2:16]([N:20]([CH2:25][C:26]1[CH:27]=[C:28]([NH2:46])[C:29]([NH:32][CH2:33][CH2:34][CH2:35][N:36]([CH3:45])[CH2:37][CH2:38]C2C=CN=CC=2)=[CH:30][CH:31]=1)[CH2:21][CH:22]([CH3:24])[CH3:23])[CH:17]([CH3:19])[CH3:18].[NH3:47]>O1CCCC1>[CH2:16]([N:20]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]2[N:32]([CH2:33][CH2:34][CH2:35][N:36]([CH3:45])[CH2:37][CH2:38][C:5]3[CH:4]=[CH:3][CH:8]=[CH:7][N:47]=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:46][C:28]=2[CH:27]=1)[CH2:21][CH:22]([CH3:23])[CH3:24])[CH:17]([CH3:18])[CH3:19]

参加物

5

反応物 3

HCID 222AmmoniaHCID 1189003,4,5-Trimethoxyphenyl isothiocyanateHCID 690281664-[(diisobutylamino)methyl]-N-(3-{methyl[2-(4-pyridinyl)ethyl]amino}propyl)-1,2-benzenediamine

生成物 1

HCID 575676335-[(diisobutylamino)methyl]-1-(3-{methyl[2-(2-pyridinyl)ethyl]amino}propyl)-N-(3,4,5-trimethoxyphenyl)-1H-benzimidazol-2-amine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

3,4,5 trimethoxyphenylisothiocyanate (57 mg, 1.2 eq) and N-methylcyclohexylcarbodiimide-N-methyl polystyrene resin (acquired from Novabiochem; load 1.69 mmol/g, 501 mg, 4 eq) are added successively to a solution of 4-[(diisobutylamino)methyl]-N-(3-{methyl[2-(4-pyridinyl)ethyl]amino}propyl)-1,2-benzenediamine (90 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. Purification by flash chromatography on silica gel (eluent: 100% dichloromethane to dichloromethane/methanol 9:1) produces the expected compound in the form of a beige foam (92 mg, 83% yield).

後処理

  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. customPurification by flash chromatography on silica gel (eluent: 100% dichloromethane to dichloromethane/methanol 9:1)

出典と根拠

ORDレコード
ord-7e6ede5030e14016ac29ef488367a60b
出典データセット
uspto-grants-2009_02
特許番号
US07495110B2

関連ノート

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