Diisopropylethylamine → HCID 59451478, compound

HRID 1874949Notes

Reaction equation

HRID 1874949 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:25][CH2:26][C:27]1[C:28]([F:44])=[C:29]([O:34][C:35]2[CH:36]=[C:37]([CH:40]=[C:41]([Cl:43])[CH:42]=2)[C:38]#[N:39])[C:30]([Cl:33])=[CH:31][CH:32]=1.[OH:45][CH2:46][CH2:47][O:48][C:49]1[CH:50]=[C:51]2[C:55](=[CH:56][CH:57]=1)[NH:54][C:53]([C:58](O)=[O:59])=[CH:52]2.CCN(C(C)C)C(C)C>O.CCOC(C)=O.CN(C=O)C>[Cl:33][C:30]1[CH:31]=[CH:32][C:27]([CH2:26][NH:25][C:58]([C:53]2[NH:54][C:55]3[C:51]([CH:52]=2)=[CH:50][C:49]([O:48][CH2:47][CH2:46][OH:45])=[CH:57][CH:56]=3)=[O:59])=[C:28]([F:44])[C:29]=1[O:34][C:35]1[CH:36]=[C:37]([C:38]#[N:39])[CH:40]=[C:41]([Cl:43])[CH:42]=1

Participants

8

Reactant 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 184556225-(2-hydroxyethoxy)-1H-indole-2-carboxylic acidHCID 594513923-{[3-(Aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile

Product 1

HCID 59451478HCID 59451478, compoundYield 37%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

HATU (0.026 g, 0.069 mmol) was added to a DMF (1 mL) solution of 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile (0.022 g, 0.069 mmol), 5-[(2-hydroxyethyl)oxy]-1H-indole-2-carboxylic acid (0.015 g, 0.069 mmol) and DIPEA (0.012 mL, 0.069 mmol). The reaction mixture was stirred for 2 h, poured into EtOAc and water and the layers separated. The organic layer was dried over MgSO4, filtered and the solvent evaporated. The residue was dissolved in MeOH and purification was accomplished by reverse-phase HPLC (water/acetonitrile with 0.1% TFA) to afford the title compound (0.013 g, 37%) as a white solid 1H NMR (400 MHz, DMSO-d6) δ ppm 11.44 (s, 1H), 8.96 (t, 1H), 7.80 (s, 1H), 7.44-7.54 (m, 3H), 7.37 (t, 1H), 7.28 (d, 1H), 7.05 (s, 2H), 6.83 (dd, 1H), 4.80 (t, 1H), 4.54 (d, 2H), 3.94 (t, 2H), 3.70 (q, 2H).

Workup

  1. customthe layers separated
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent evaporated
  5. dissolutionThe residue was dissolved in MeOH
  6. custompurification

Sources & evidence

ORD record
ord-b24e5587e8ec4973b8de72a5a8666e24
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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