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

HRID 1714007노트

반응식

HRID 1714007 반응식
[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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-835222a084b24f8e92ff78cb1736c6f4
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795247B2

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