Diisopropylethylamine → tert-butyl-2-bromo-1-(2-{(2-bromo-5-chlorobenzyl)[2-(dimethylamino)ethyl]amino}-2-oxoethyl)-3-cyclohexyl-1H-indole-6-carboxylate

HRID 1714007ノート

反応式

HRID 1714007 の反応式
[Br:1][C:2]1[N:3]([CH2:24][C:25](O)=[O:26])[C:4]2[C:9]([C:10]=1[CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[CH:8][CH:7]=[C:6]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:5]=2.[Br:28][C:29]1[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][C:30]=1[CH2:31][NH:32][CH2:33][CH2:34][N:35]([CH3:37])[CH3:36].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[C:20]([O:19][C:17]([C:6]1[CH:5]=[C:4]2[C:9]([C:10]([CH:11]3[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]3)=[C:2]([Br:1])[N:3]2[CH2:24][C:25]([N:32]([CH2:31][C:30]2[CH:38]=[C:39]([Cl:42])[CH:40]=[CH:41][C:29]=2[Br:28])[CH2:33][CH2:34][N:35]([CH3:37])[CH3:36])=[O:26])=[CH:8][CH:7]=1)=[O:18])([CH3:21])([CH3:23])[CH3:22]

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66160827N'-(2-bromo-5-chlorobenzyl)-N,N-dimethylethane-1,2-diamineHCID 68509336[2-bromo-6-(tert-butoxycarbonyl)-3-cyclohexyl-1H-indol-1-yl]acetic acid

生成物 1

HCID 68507168tert-butyl-2-bromo-1-(2-{(2-bromo-5-chlorobenzyl)[2-(dimethylamino)ethyl]amino}-2-oxoethyl)-3-cyclohexyl-1H-indole-6-carboxylate収率 56%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of [2-bromo-6-(tert-butoxycarbonyl)-3-cyclohexyl-1H-indol-1-yl]acetic acid (from Step 7, 1 eq) in DCM (0.07 M), N′-(2-bromo-5-chlorobenzyl)-N,N-dimethylethane-1,2-diamine (from Step 3, 2.1 eq), DIPEA (3 eq) and HATU (2 eq) were added and the mixture stirred at RT overnight. The solution was diluted with DCM and washed with HCl (1 N), a saturated aqueous solution of NaHCO3 and brine, dried (Na2SO4), filtered and concentrated in vacuo to afford the title compound (56%) that was used in the next step without further purification; MS (ES+) m/z 710 (M+H)+.

後処理

  1. washwashed with HCl (1 N)
  2. dry with materiala saturated aqueous solution of NaHCO3 and brine, dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-835222a084b24f8e92ff78cb1736c6f4
出典データセット
uspto-grants-2010_09
特許番号
US07795247B2

反応ノート

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