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

HRID 1661503

反応式

HRID 1661503 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-a1ab6a61c1e54f208497af99afec16a7
出典データセット
uspto-grants-2011_10
特許番号
US08030344B2

関連ノート

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