2-Pyrazinecarboxylic acid → Pyrazine-2-carboxylic acid 4-(4-amino-2-methyl-quinolin-6-ylcarbamoyl)-benzylamide

HRID 19513

반응식

HRID 19513 반응식
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.[NH2:32][CH2:33][C:34]1[CH:54]=[CH:53][C:37]([C:38]([NH:40][C:41]2[CH:42]=[C:43]3[C:48](=[CH:49][CH:50]=2)[N:47]=[C:46]([CH3:51])[CH:45]=[C:44]3[NH2:52])=[O:39])=[CH:36][CH:35]=1.C(N1CCOCC1)C>CN(C=O)C>[NH2:52][C:44]1[C:43]2[C:48](=[CH:49][CH:50]=[C:41]([NH:40][C:38]([C:37]3[CH:53]=[CH:54][C:34]([CH2:33][NH:32][C:7]([C:2]4[CH:3]=[N:4][CH:5]=[CH:6][N:1]=4)=[O:9])=[CH:35][CH:36]=3)=[O:39])[CH:42]=2)[N:47]=[C:46]([CH3:51])[CH:45]=1

참가 물질

6

반응물 4

HCID 10472-Pyrazinecarboxylic acidHCID 7525EthylmorpholineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178646234-Aminomethyl-N-(4-amino-2-methyl-quinolin-6-yl)-benzamide

생성물 1

HCID 12110091Pyrazine-2-carboxylic acid 4-(4-amino-2-methyl-quinolin-6-ylcarbamoyl)-benzylamide수율 111.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 10.5 mg (0.08 mmol) of 2-pyrazinecarboxylic acid in 1 ml of DMF were added 27.9 mg (0.085 mmol) TOTU. After 15 min at room temperature 55 mg (0.085 mmol) of 4-Aminomethyl-N-(4-amino-2-methyl-quinolin-6-yl)-benzamide and 39 mg (0.34 mmol) of N-ethylmorpholine were added. After 24 h stirring at room temperature the solution was evaporated and the residue was treated with acetonitrile and water containing 0.005% trifluoroacetic acid. The precipitate was filtered to give 36.7 mg (71%) of the title compound. MS 413.42 (M+1)+, 1H-NMR (DMSO-d6) δ 2.58 (s, 3H), 4.60 (d, 2H), 6.58 (s, NH), 7.55 (d, 2H), 7.81 (d, 1H), 8.00 (m, 3H), 8.65 (br.s., NH2), 8.78 (m, 2H), 8.90 (m, 1H), 9.20 (s, 1H), 9.62 (m, 1H), 10.80 (s, NH), 13.38 (br.s., NH).

후처리

  1. customwas evaporated
  2. additionthe residue was treated with acetonitrile and water containing 0.005% trifluoroacetic acid
  3. filtrationThe precipitate was filtered

출처 및 근거

ORD 기록
ord-e4b1890606394513a607daaa28ddf54f
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745443B2

연결된 노트

불러오는 중…