Diisopropylethylamine → HCID 68349189, compound

HRID 1850071Notes

Reaction equation

HRID 1850071 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:10][N:11]3[CH2:14][C:13](=[CH:15][C:16]4[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][C:17]=4[Cl:25])[CH2:12]3)[CH:8]=2)[CH:3]=[CH:2]1.CCN(C(C)C)C(C)C.[C:35]([O:39][C:40](=[O:49])[NH:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=1[NH2:48])([CH3:38])([CH3:37])[CH3:36].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:10][N:11]3[CH2:14][C:13](=[CH:15][C:16]4[CH:24]=[CH:23][C:19]([C:20]([NH:48][C:43]5[CH:44]=[CH:45][CH:46]=[CH:47][C:42]=5[NH:41][C:40](=[O:49])[O:39][C:35]([CH3:38])([CH3:36])[CH3:37])=[O:21])=[CH:18][C:17]=4[Cl:25])[CH2:12]3)[CH:8]=2)[CH:3]=[CH:2]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 676311N-(tert-Butoxycarbonyl)-1,2-phenylenediamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68294316HCID 68294316, compound

Product 1

HCID 68349189HCID 68349189, compoundYield 49.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-((1-((1H-indol-6-yl)methyl)azetidin-3-ylidene)methyl)-3-chlorobenzoic acid (0.26 g, 0.74 mmol) in DCM (25 mL) was added DIPEA (0.29 g, 2.22 mmol), tert-butyl-2-aminophenylcarbamate (0.27 g, 1.18 mmol) and HATU (0.37 g, 0.96 mmol). The reaction mixture was stirred overnight at room temperature under a nitrogen atmosphere. After completion of the reaction as indicated by HPLC, the mixture was washed with saturated sodium bicarbonate (2×20 mL) and brine (1×15 mL). It was dried (Na2SO4), filtered and evaporated to give the crude product which was purified by column chromatography (10% MeOH: 90% DCM). After evaporation of pooled fractions of pure product, tert-butyl (2-(4-((1-((1H-indol-6-yl)methyl)azetidin-3-ylidene)methyl)-3-chlorobenzamido)phenyl)carbamate (0.2 g) was isolated as an off-white solid. ES+(M+H)+ 543.

Workup

  1. customAfter completion of the reaction
  2. washthe mixture was washed with saturated sodium bicarbonate (2×20 mL) and brine (1×15 mL)
  3. dry with materialIt was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customto give the crude product which
  7. customwas purified by column chromatography (10% MeOH: 90% DCM)
  8. customAfter evaporation of pooled fractions of pure product

Sources & evidence

ORD record
ord-95500695a13541538e0903fa205afcef
Source dataset
uspto-grants-2015_02
Patent number
US08957066B2

Reaction notes

Loading…