Diisopropylethylamine → HCID 59451347, compound

HRID 1874821Notes

Reaction equation

HRID 1874821 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]([O:49][C:50]([NH:52][C:53]1[CH:54]=[CH:55][CH:56]=[C:57]2[C:61]=1[NH:60][C:59]([C:62](O)=[O:63])=[CH:58]2)=[O:51])([CH3:48])[CH3:47].CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:33][C:30]1[CH:31]=[CH:32][C:27]([CH2:26][NH:25][C:62]([C:59]2[NH:60][C:61]3[C:57]([CH:58]=2)=[CH:56][CH:55]=[CH:54][C:53]=3[NH:52][C:50](=[O:51])[O:49][C:46]([CH3:47])([CH3:45])[CH3:48])=[O:63])=[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

6

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 57901795HCID 57901795, compoundHCID 594513923-{[3-(Aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile

Product 1

HCID 59451347HCID 59451347, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

HATU (0.055 g, 0.145 mmol) was added to a solution of 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile (0.030 g, 0.096 mmol), 7-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-1H-indole-2-carboxylic acid (0.026 g, 0.096 mmol) and DIPEA (0.025 mL, 0.145 mmol) in DMF (1 mL). The mixture was stirred at RT overnight then extracted with water and ethyl acetate. The organic layer was separated, dried over sodium sulfate, and concentrated. The residue was purified by column chromatography (hexane/EtOAc) to give the title compound (0.027 g, 44%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 11.59 (s, 1H), 9.32 (s, 1H), 9.07 (t, 1H), 7.81 (s, 1H), 7.67-7.77 (m, 1H), 7.44-7.57 (m, 3H), 7.39 (t, 1H), 7.27 (d, 1H), 7.17 (d, 1H), 6.96 (t, 1H), 4.57 (d, 2H), 1.5 (s, 9H). MS: m/z 569 (M).

Workup

  1. extractionthen extracted with water and ethyl acetate
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-91da97172dfd43fe8a5261b47daa88e5
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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