Sodium Carbonate → 3-Amino-6-[4-(dimethylcarbamoyl)phenyl]pyrazine-2-carboxylic acid

HRID 78678

반응식

HRID 78678 반응식
[NH2:1][C:2]1[C:3]([C:9]([O:11]C)=[O:10])=[N:4][C:5](Br)=[CH:6][N:7]=1.[CH3:13][N:14]([CH3:26])[C:15]([C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1)=[O:16].C([O-])([O-])=O.[Na+].[Na+]>C(#N)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:1][C:2]1[C:3]([C:9]([OH:11])=[O:10])=[N:4][C:5]([C:20]2[CH:21]=[CH:22][C:17]([C:15](=[O:16])[N:14]([CH3:13])[CH3:26])=[CH:18][CH:19]=2)=[CH:6][N:7]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 227251Methyl 3-Amino-6-bromopyrazine-2-carboxylateHCID 35037674-(Dimethylcarbamoyl)phenylboronic Acid

생성물 1

HCID 594717503-Amino-6-[4-(dimethylcarbamoyl)phenyl]pyrazine-2-carboxylic acid수율 65%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

Methyl 3-amino-6-bromo-pyrazine-2-carboxylate (6.01 g, 25.9 mmol, 1.0 Eq.), 4-(dimethylcarbamoyl)phenylboronic acid (5.00 g, 25.9 mmol, 1.0 Eq.), Na2CO3 (5.49 g, 51.8 mmol, 2.0 Eq.) and Pd(PPh3)4 (2.99 g, 2.59 mmol, 0.1 Eq.) in acetonitrile (30 mL) and water (30 mL) were heated at 90° C. for 16 hours. After cooling to ambient temperature the precipitate was removed by filtration. The aqueous filtrate was acidified to pH4 by addition of 1M HCl and then extracted with dichloromethane (3×20 mL), dried over MgSO4 and concentrated in vacuo to give the sub-title product as a yellow solid (2.42 g, 65% Yield). 1H NMR (400.0 MHz, DMSO) δ 2.95 (3H, br s), 3.00 (3H, br s), 7.49-7.51 (2H, m), 7.58 (2H, br s), 8.15 92H, d), 8.95 (1H, s), 13.25 (1H, br s) ppm; MS (ES+) 287.13.

후처리

  1. customwas removed by filtration
  2. additionThe aqueous filtrate was acidified to pH4 by addition of 1M HCl
  3. extractionextracted with dichloromethane (3×20 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-8a9076b3af6e47d9ac74300c7beef41a
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841308B2

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