O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → N-[4-Methoxy-3-(4-bromophenyl)aminocarbonyl-phenyl]-2-chloro-5-(tert-butylcarbonylamino)methyl-benzamide

HRID 1846083ノート

反応式

HRID 1846083 の反応式
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[Cl:23][C:24]1[CH:32]=[CH:31][C:30]([CH2:33][NH:34][C:35]([C:37]([CH3:40])([CH3:39])[CH3:38])=[O:36])=[CH:29][C:25]=1[C:26]([OH:28])=O.[Br:41][C:42]1[CH:47]=[CH:46][C:45]([NH:48][C:49](=[O:59])[C:50]2[CH:55]=[C:54]([NH2:56])[CH:53]=[CH:52][C:51]=2[O:57][CH3:58])=[CH:44][CH:43]=1>CN(C=O)C>[CH3:58][O:57][C:51]1[CH:52]=[CH:53][C:54]([NH:56][C:26](=[O:28])[C:25]2[CH:29]=[C:30]([CH2:33][NH:34][C:35]([C:37]([CH3:40])([CH3:39])[CH3:38])=[O:36])[CH:31]=[CH:32][C:24]=2[Cl:23])=[CH:55][C:50]=1[C:49]([NH:48][C:45]1[CH:46]=[CH:47][C:42]([Br:41])=[CH:43][CH:44]=1)=[O:59]

参加物

5

反応物 3

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 584832082-Chloro-5-[(2,2-dimethylpropanamido)methyl]benzoic acidHCID 61090759N-(4-Bromophenyl)-2-methoxy-5-amino-benzoic acid amide

生成物 1

HCID 51347356N-[4-Methoxy-3-(4-bromophenyl)aminocarbonyl-phenyl]-2-chloro-5-(tert-butylcarbonylamino)methyl-benzamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

TBTU (40 mg, 0.125 mmol) in 0.25 mL DMF was added to 2-chloro-5-(tert-butylcarbonylamino)methyl-benzoic acid (34 mg, 0.125 mmol), followed by 50 μL TEA and the mixture was stirred for 5 min. Then N-(4-bromophenyl)-2-methoxy-5-amino-benzoic acid amide in 0.25 mL DMF was added and it was stirred overnight. The crude mixture was filtered through aluminium oxide and the solid phase was washed 4× with 1 mL DMF/MeOH 9:1. The combined organic phase was concentrated i.vac. dissolved in Acetonitrile/HCOOH, filtered and dried via lyophilisation to furnish the title compound.

後処理

  1. stirringit was stirred overnight
  2. filtrationThe crude mixture was filtered through aluminium oxide
  3. washthe solid phase was washed 4× with 1 mL DMF/MeOH 9:1
  4. concentrationThe combined organic phase was concentrated i.vac
  5. dissolutiondissolved in Acetonitrile/HCOOH
  6. filtrationfiltered
  7. customdried via lyophilisation

出典と根拠

ORDレコード
ord-3a065fc8e86647b995c48bfb875bb2f1
出典データセット
uspto-grants-2015_02
特許番号
US08951999B2

反応ノート

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