Methanol → 4-(4-Amino-6-(5-chloro-1H-indol-4-ylmethyl)-(1,3,5)triazin-2-ylamino)-benzonitrile

HRID 843636ノート

反応式

HRID 843636 の反応式
CO.[NH2:3][C:4]1[N:9]=[C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)[N:7]=[C:6]([CH2:19][C:20]2[C:28]([Cl:29])=[CH:27][CH:26]=[C:25]3[C:21]=2[CH:22]=[CH:23][N:24]3S(C2C=CC(C)=CC=2)(=O)=O)[N:5]=1.C([O-])([O-])=O.[K+].[K+]>O>[NH2:3][C:4]1[N:5]=[C:6]([CH2:19][C:20]2[C:28]([Cl:29])=[CH:27][CH:26]=[C:25]3[C:21]=2[CH:22]=[CH:23][NH:24]3)[N:7]=[C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)[N:9]=1

参加物

5

反応物 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 22281693HCID 22281693、化合物

生成物 1

HCID 4485334-(4-Amino-6-(5-chloro-1H-indol-4-ylmethyl)-(1,3,5)triazin-2-ylamino)-benzonitrile収率 45%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

Methanol (120 ml) was added to a mixture of intermediate (5) (2.35 g) and K2CO3 (9.19 g) in water (40 ml). The resulting reaction mixture was stirred and refluxed for 19 hours under argon. Water (120 ml) was added, the precipitate was filtered off and purified by column chromatography over silica gel (eluent:DCM/2-propanone 0/10). Two desired fractions were collected and their solvent was evaporated. The first fraction group was slurried in ACN, cooled, filtered off and dried, yielding 0.75 g (45%, white solid) of 4-[[4-amino-6-[(5-chloro-1H-indol-4-yl)methyl]-1,3,5-triazin-2-yl]amino]benzonitrile (compound 8, mp. 267-268° C.). The second column fraction group yielded 0.15 g of 4-[[4-amino-6-[(5-chloro-IH-indol-4-yl)methyl]-1,3,5-triazin-2-yl]amino]benzamide (compound 9). After 24 hours at RT the aqueous filtrate was filtered to give 0.25 g of compound (9). The two fractions of compound 9 were combined, dissolved in 500 ml of refluxing methanol, hot filtered, the filtrate concentrated to 50 ml, cooled and filtered, then dried, yielding 0.25 g (14%) of 4-[[4-amino-6-[(5-chloro-1H-indol-4-yl)methyl]-1,3,5-triazin-2-yl]amino]benzamide (compound 9, mp. 204-205° C.).

後処理

  1. customThe resulting reaction mixture
  2. temperaturerefluxed for 19 hours under argon
  3. filtrationthe precipitate was filtered off
  4. custompurified by column chromatography over silica gel (eluent:DCM/2-propanone 0/10)
  5. customTwo desired fractions were collected
  6. customtheir solvent was evaporated
  7. temperaturecooled
  8. filtrationfiltered off
  9. customdried

出典と根拠

ORDレコード
ord-5b1b74bfc149434e92aca932b83d5536
出典データセット
uspto-grants-2002_04
特許番号
US06380194B1

反応ノート

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