Diisopropylethylamine → HCID 59451544, compound

HRID 1874813Notes

Reaction equation

HRID 1874813 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.[CH3:45][C:46]1[CH:47]=[CH:48][CH:49]=[C:50]2[C:54]=1[NH:53][C:52]([C:55](O)=[O:56])=[CH:51]2.CCN(C(C)C)C(C)C>CN(C=O)C.C(OCC)(=O)C.O>[Cl:33][C:30]1[CH:31]=[CH:32][C:27]([CH2:26][NH:25][C:55]([C:52]2[NH:53][C:54]3[C:50]([CH:51]=2)=[CH:49][CH:48]=[CH:47][C:46]=3[CH3:45])=[O:56])=[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 32961197-methyl-1H-indole-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 594513923-{[3-(Aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile

Product 1

HCID 59451544HCID 59451544, compoundYield 57.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

HATU (0.072 g, 0.19 mmol) was added to a solution of 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile (0.040 g, 0.13 mmol), 7-methyl-1H-indole-2-carboxylic acid (0.033 g, 0.19 mmol) and DIPEA (0.033 mL, 0.19 mmol) in DMF (1 mL). After 1 h, the reaction mixture was diluted with ethyl acetate and water. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by column chromatography (hexane/EtOAc) to give a sticky solid, which was triturated with methanol and dried under vacuum to give the title compound (0.035 g, 57%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 11.38 (s, 1H), 8.99 (t, 1H), 7.81 (s, 1H), 7.26-7.63 (m, 5H), 7.15 (d, 1H), 6.68-7.06 (m, 2H), 4.57 (d, 2H), 2.21-2.69 (s, 3H). MS: m/z 468 (M+1).

Workup

  1. washThe organic layer was washed with water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography (hexane/EtOAc)
  5. customto give a sticky solid, which
  6. customwas triturated with methanol
  7. customdried under vacuum

Sources & evidence

ORD record
ord-c9f822e1407d4dcdb438202e986ca13b
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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