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

HRID 552199

반응식

HRID 552199 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 284Formic Acid용매HCID 1049Pyridine용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c0cda17c42564ad1b899e032af4ceac4
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07951801B2

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