Triethylamine → tert-Butyl 2-(6-chloronicotinamido)phenylcarbamate

HRID 1661503

반응식

HRID 1661503 반응식
[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH2:14])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[Cl:23][C:24]1[CH:32]=[CH:31][C:27]([C:28](O)=[O:29])=[CH:26][N:25]=1>CC#N>[Cl:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([NH:14][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][C:6](=[O:15])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:29])=[CH:26][N:25]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 792226-Chloronicotinic acidHCID 676311N-(tert-Butoxycarbonyl)-1,2-phenylenediamine

생성물 1

HCID 57717462tert-Butyl 2-(6-chloronicotinamido)phenylcarbamate수율 92%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To solution of (2-amino-phenyl)-carbamic acid tert-butyl ester (22) (Seto, C. T.; Mathias, J. P.; Whitesides, G. M.; J. Amer. Chem. Soc., (1993), 115, 1321-1329.) (1.56 g, 7.49 mmol) in MeCN (40 mL) is added triethylamine (2.60 mL, 18.7 mmol) and 6-chloronicotinic acid (1.42 g 8.99 mmol). The mixture is stirred for 18 h at r.t. Upon completion of the reaction, the solvent is removed in vacuo and the residue is partitioned between EtOAc and an NH4Cl solution. The organic phase is collected and the aqueous layer is then extracted with EtOAc; the combined organic layers are washed with brine, dried over MgSO4 and evaporated. The residue is purified by flash chromatography using EtOAc/Hexane (a gradient of 20:80 to 50:50) as an eluent, to afford the title compound 94 (2.39 g, 92% yield). 1H NMR (DMSO-d6) δ(ppm): 10.01 (s, 1H), 8.96 (d, J=2.0 Hz, 1H), 8.71 (s, 1H), 8.35 (dd, J=8.4, 2.4 Hz, 1H), 7.73 (d, J=8.0 Hz, 1H), 7.62 (d, J=8.0 Hz, 1H), 7.48 (d, J=7.6 Hz, 1H), 7.22 (td, J=7.8, 1.4 Hz, 1H), 7.13 (t, J=7.6 Hz, 1H), 1.44 (s, 9H). LRMS (ESI): (calc) 347.10 (found) 370.1 (M+Na+).

후처리

  1. customUpon completion of the reaction
  2. customthe solvent is removed in vacuo
  3. customthe residue is partitioned between EtOAc
  4. customThe organic phase is collected
  5. extractionthe aqueous layer is then extracted with EtOAc
  6. washthe combined organic layers are washed with brine
  7. dry with materialdried over MgSO4
  8. customevaporated
  9. customThe residue is purified by flash chromatography

출처 및 근거

ORD 기록
ord-a1ab6a61c1e54f208497af99afec16a7
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030344B2

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