2-Chloroaniline → N-(2-Chlorophenyl)-6-(3-ethylureido)-4-(phenylamino)nicotinamide

HRID 2174237ノート

反応式

HRID 2174237 の反応式
[CH2:1]([NH:3][C:4](=[O:22])[NH:5][C:6]1[CH:14]=[C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9]([C:10]([OH:12])=O)=[CH:8][N:7]=1)[CH3:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[Cl:56][C:57]1[CH:63]=[CH:62][CH:61]=[CH:60][C:58]=1[NH2:59]>CN(C=O)C>[Cl:56][C:57]1[CH:63]=[CH:62][CH:61]=[CH:60][C:58]=1[NH:59][C:10](=[O:12])[C:9]1[C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:14][C:6]([NH:5][C:4]([NH:3][CH2:1][CH3:2])=[O:22])=[N:7][CH:8]=1

参加物

6

反応物 4

HCID 72402-ChloroanilineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 896500056-(3-Ethylureido)-4-(phenylamino)nicotinic acid

生成物 1

HCID 71620848N-(2-Chlorophenyl)-6-(3-ethylureido)-4-(phenylamino)nicotinamide収率 15.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To an ice-cold solution of 6-(3-ethylureido)-4-(phenylamino)nicotinic acid (50 mg, 0.16 mmol, 1.0 eq) in DMF (2.0 mL) was added HBTU (91 mg, 0.24 mmol, 1.50 eq) followed by DIPEA (62 mg, 0.48 mmol, 3.0 eq) and finally 2-chloroaniline (24 mg, 0.19 mmol, 1.20 eq). The resulting reaction mixture was stirred overnight at room temperature. The reaction mass was then poured onto ice-cold water followed by extraction with EtOAc (3×20 mL). The organics were combined, washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified over silica gel (60-120 M, 1-2.5% MeOH-DCM) to obtain Compound 9 (10 mg, 15%). NMR (300 MHz, DMSO-d6): δ 10.17 (br s, 1H), 10.08 (br s, 1H), 9.12 (s, 1H), 8.67 (s, 1H), 7.87 (m, 1H), 7.56 (m, 1H), 7.24-7.40 (m, 8H), 7.15 (m, 1H), 3.14 (m, 2H), 1.06 (t, J=7.20 Hz, 3H). [M+H]+ m/z=410.15.

後処理

  1. customThe resulting reaction mixture
  2. additionThe reaction mass was then poured onto ice-cold water
  3. extractionfollowed by extraction with EtOAc (3×20 mL)
  4. washwashed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified over silica gel (60-120 M, 1-2.5% MeOH-DCM)

出典と根拠

ORDレコード
ord-32f3c806e63a42758ce87979e7617abd
出典データセット
uspto-grants-2015_06
特許番号
US09060515B2

反応ノート

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