Diisopropylethylamine → 2-Chloro-N-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]phenyl}methyl)-4-(methylsulfonyl)benzamide

HRID 1874770

反応式

HRID 1874770 の反応式
[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([Cl:19])=[C:7]([O:9][C:10]2[CH:11]=[C:12]([CH:15]=[C:16]([Cl:18])[CH:17]=2)[C:13]#[N:14])[CH:8]=1.[Cl:20][C:21]1[CH:29]=[C:28]([S:30]([CH3:33])(=[O:32])=[O:31])[CH:27]=[CH:26][C:22]=1[C:23](O)=[O:24].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:20][C:21]1[CH:29]=[C:28]([S:30]([CH3:33])(=[O:32])=[O:31])[CH:27]=[CH:26][C:22]=1[C:23]([NH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([Cl:19])=[C:7]([O:9][C:10]2[CH:11]=[C:12]([C:13]#[N:14])[CH:15]=[C:16]([Cl:18])[CH:17]=2)[CH:8]=1)=[O:24]

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 7358632-Chloro-4-(methylsulfonyl)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 594514053-{[5-(Aminomethyl)-2-chlorophenyl]oxy}-5-chlorobenzonitrile

生成物 1

HCID 594516222-Chloro-N-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]phenyl}methyl)-4-(methylsulfonyl)benzamide収率 69.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

2-Chloro-N-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]phenyl}methyl)-4-(methylsulfonyl)benzamide was prepared in a similar manner as described herein from 3-{[5-(aminomethyl)-2-chlorophenyl]oxy}-5-chlorobenzonitrile (0.025 g, 0.085 mmol), 2-chloro-4-(methylsulfonyl)benzoic acid, (0.03 g, 0.13 mmol), HATU (0.05 g, 0.13 mmol), DIPEA (0.025 mL, 0.13 mmol) and DMF (1 mL). The crude material was purified by Reverse-Phase HPLC (water/acetonitrile with 0.1% TFA). The desired fractions were neutralized and extracted with EtOAc. The organic extracts were combined, dried over Na2SO4, filtered and evaporated to afford the title compound (0.030 g, 69%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 9.20 (t, 1H), 8.02 (d, 1H), 7.92 (dd, 1H), 7.83 (d, 1H), 7.69 (d, 1H), 7.62 (d, 1H), 7.48 (d, 1H), 7.41 (t, 1H), 7.31 (dd, 1H), 7.23 (d, 1H), 4.46 (d, 2H), 3.30 (s, 3H). MS: m/z 508.9 (M+1).

後処理

  1. custom2-Chloro-N-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]phenyl}methyl)-4-(methylsulfonyl)benzamide was prepared in a similar manner
  2. customThe crude material was purified by Reverse-Phase HPLC (water/acetonitrile with 0.1% TFA)
  3. extractionextracted with EtOAc
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

出典と根拠

ORDレコード
ord-858eae7b3e5a4760894c69cf80af5efb
出典データセット
uspto-grants-2012_11
特許番号
US08304419B2

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