1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(6-chloro-7-fluoro-9H-beta-carbolin-8-yl)-2-methyl-nicotinamide

HRID 552199

反応式

HRID 552199 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH2:16])[C:14]=1[F:15])[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1.[CH3:17][C:18]1[N:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](O)=[O:21].CCN=C=NCCCN(C)C.C1C(NN)=NN=C(N(CCO)CCO)C=1.Cl.Cl>N1C=CC=CC=1.C(O)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH:16][C:20](=[O:21])[C:19]3[CH:23]=[CH:24][CH:25]=[N:26][C:18]=3[CH3:17])[C:14]=1[F:15])[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1

参加物

7

反応物 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 168701Oxdralazine dihydrochlorideHCID 6433732-Methylnicotinic acidHCID 671655216-chloro-7-fluoro-9H-beta-carbolin-8-ylamine

生成物 1

HCID 11337193N-(6-chloro-7-fluoro-9H-beta-carbolin-8-yl)-2-methyl-nicotinamide

試薬・触媒・溶媒 2

HCID 284Formic Acid溶媒HCID 1049Pyridine溶媒

反応条件

温度
100 °C

実験手順

A solution of 6-chloro-7-fluoro-9H-β-carbolin-8-ylamine (100 mg, 0.424 mmol) in pyridine (2.5 ml) was stirred at RT. 2-methyl nicotinic acid (70 mg, 0.509 mmol) was added, followed by EDCI (130 mg, 0.678 mmol). The suspension was stirred at 100° C. for a day. The pyridine was removed under reduced pressure and the resulting dark oil was triturated with saturated aqueous NaHCO3. The precipitate which formed was filtered and washed with MeOH. The material was treated with 2M HCl in Et2O to yield a gray solid, the di-HCl salt N-(6-chloro-7-fluoro-9H-β-carbolin-8-yl)-2-methyl-nicotinamide (110 mg). 1H-NMR (300 MHz, DMSO-d6): δ 13.15 (s, 1); 11.03 (s, 1); 9.33 (s, 1); 8.99-8.97 (m, 1); 8.92-8.89 (m, 1); 8.79-8.73 (m, 2); 8.50 (m, 1); 7.70 (m, 1); 2.80 (s, 3). HCOOH standard conditions. DAD Rf=0.91 min. MS (M+H+): 355.

後処理

  1. customThe pyridine was removed under reduced pressure
  2. customthe resulting dark oil was triturated with saturated aqueous NaHCO3
  3. customThe precipitate which formed
  4. filtrationwas filtered
  5. washwashed with MeOH
  6. additionThe material was treated with 2M HCl in Et2O
  7. customto yield a gray solid

出典と根拠

ORDレコード
ord-c0cda17c42564ad1b899e032af4ceac4
出典データセット
uspto-grants-2011_05
特許番号
US07951801B2

関連ノート

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