Diisopropylethylamine → HCID 24947293、化合物

HRID 1643318ノート

反応式

HRID 1643318 の反応式
[NH:1]([C:8](=[O:30])[CH2:9][N:10]([CH2:20][C:21](=[O:29])[NH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:11]1[CH:19]=[CH:18][C:14]([C:15](O)=[O:16])=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.[NH2:67][C:68]1[CH:69]=[C:70]([C:82]2[CH:87]=[CH:86][CH:85]=[CH:84][CH:83]=2)[CH:71]=[CH:72][C:73]=1[NH:74]C(=O)OC(C)(C)C>CCOC(C)=O.C(Cl)Cl.CN(C=O)C>[NH2:74][C:73]1[CH:72]=[CH:71][C:70]([C:82]2[CH:83]=[CH:84][CH:85]=[CH:86][CH:87]=2)=[CH:69][C:68]=1[NH:67][C:15](=[O:16])[C:14]1[CH:18]=[CH:19][C:11]([N:10]([CH2:20][C:21]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:29])[CH2:9][C:8](=[O:30])[NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:12][CH:13]=1

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 57717454N-(3-Amino[1,1'-biphenyl]-4-yl)-carbamic Acid tert-Butyl EsterHCID 57857116HCID 57857116、化合物

生成物 1

HCID 24947293HCID 24947293、化合物

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 22350042dichloromethane N,N-dimethylformamide溶媒

実験手順

To a solution of 4-[bis(2-anilino-2-oxoethyl)amino]benzoic acid (40 mg, 0.099 mmol) in 2:1 CH2Cl2/DMF was added BOP (66 mg, 0.149 mmol), Hunigs base (26 μL, 0.149 mmol) and tert-butyl (3-aminobipheyl-4-yl)carbamate (56 mg, 0.199 mmol) and the reaction was allowed to stir at room temperature for 12 hours. The crude reaction mixture was diluted with EtOAc (20 mL) and then washed with sat.'d aq. NaHCO3 (1×10 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was purified by reverse-phase chromatography (30-100% MeCN/H2O with 0.05% TFA). The appropriate fractions were combined, diluted with EtOAc (20 mL) and washed with sat.'d aq. NaHCO3 (1×10 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo and gave the desired N-(2-aminophenyl)-4-[bis(2-anilino-2-oxoethyl)amino]benzamide: 1H NMR (600 MHz, MeOH-d4) δ 7.93 (d, J=8.9 Hz, 2H), 7.66 (dt, J=8.6, 1.5 Hz, 4H), 7.52 (d, J=7.2 Hz, 2H), 7.44 (s, 1H), 7.30 (m, 8H), 7.10 (t, J=7.8 Hz, 2H), 6.96 (d, J=7.8 Hz, 1H), 6.74 (d, J=9.1 Hz, 2H), 6.53 (t, J=7.2 Hz, 1H), 4.79 (s, 2H), 4.42 (s, 4H); MS: cal'd 570.2 (MH+), exp 570.2 (MH+).

後処理

  1. customThe crude reaction mixture
  2. washwashed with sat.'d aq. NaHCO3 (1×10 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by reverse-phase chromatography (30-100% MeCN/H2O with 0.05% TFA)
  7. additiondiluted with EtOAc (20 mL)
  8. washwashed with sat.'d aq. NaHCO3 (1×10 mL)
  9. dry with materialThe organic layer was dried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-35e8edb272df4466b39c627ccc473d00
出典データセット
uspto-grants-2012_02
特許番号
US08119685B2

反応ノート

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