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Triethylamine → 2-Amino-6-chloronicotinamide

HRID 2201554
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HRID 2201554 반응식
[NH2:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C1C=CC2N(O)N=[N:18]C=2C=1.CCN=C=NCCCN(C)C.C(N(CC)CC)C.[NH4+].[Cl-]>CN(C=O)C>[NH2:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:18])=[O:5]
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참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 122639922-Amino-6-chloronicotinic acid

생성물 1

HCID 226076432-Amino-6-chloronicotinamide수율 81%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2-amino-6-chloronicotinic acid (1.0 g, 5.79 mmol), HOBT (932 mg, 6.95 mmol) and EDCI (2.22 g, 11.6 mmol) in 15 mL of DMF was added triethylamine (5.86 g, 57.9 mmol) and NH4Cl (1.55 g, 28.9 mmol). Then the mixture was stirred at room temperature for 16 h. The solution was concentrated in vacuo to remove DMF and the residue was suspended in saturated NaHCO3 Finally the 2-amino-6-chloronicotinamide (800 mg, yield: 81%) was obtained by filtration without further purification. 1H-NMR (DMSO-d6, 400 MHz) δ 7.95 (d, J=8.4 Hz, 1H), 7.62 (s, 2H), 7.39 (s, 2H), 6.59 (d, J=8.4 Hz, 1H). MS (M+H)+: 172/174.

후처리

  1. concentrationThe solution was concentrated in vacuo
  2. customto remove DMF

출처 및 근거

ORD 기록
ord-caab586f5e46466388e8f3efb3af5ecc
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09364482B2

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