Diisopropylethylamine → HCID 59451614, compound

HRID 1874944Notes

Reaction equation

HRID 1874944 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][S:46][CH2:47][CH2:48][O:49][C:50]1[CH:51]=[C:52]2[C:56](=[CH:57][CH:58]=1)[NH:55][C:54]([C:59](O)=[O:60])=[CH:53]2.CCN(C(C)C)C(C)C>CN(C=O)C.O.CCOC(C)=O>[Cl:33][C:30]1[CH:31]=[CH:32][C:27]([CH2:26][NH:25][C:59]([C:54]2[NH:55][C:56]3[C:52]([CH:53]=2)=[CH:51][C:50]([O:49][CH2:48][CH2:47][S:46][CH3:45])=[CH:58][CH:57]=3)=[O:60])=[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 594513923-{[3-(Aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrileHCID 68480834HCID 68480834, compound

Product 1

HCID 59451614HCID 59451614, compoundYield 52%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

HATU (0.055 g, 0.145 mmol) was added as a solid to a solution of 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile (0.045 g, 0.145 mmol), 5-{[2-(methylthio)ethyl]oxy}-1H-indole-2-carboxylic acid (0.036 g, 0.145 mmol) and DIPEA (0.025 mL, 0.145 mmol) in DMF (1 mL). After 2 hours the reaction mixture was poured into EtOAc and water and the layers were 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 (0.041 g, 52%) as a white solid. 1H NMR (400 MHz, Acetone-d6) δ ppm 10.64 (br. s., 1H), 8.28 (br. s., 1H), 7.61 (s, 1H), 7.33-7.51 (m, 5H), 7.00-7.13 (m, 2H), 6.89 (dd, 1H), 4.66 (d, 2 H), 4.15 (t, 2H), 2.85 (t, 2H), 2.17 (s, 3H). LC-MS (ES+) m/z 544.4 [M+H].

Workup

  1. customthe layers were 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-c97e0041ba6547babc301f15d474af63
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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