Diisopropylethylamine → HCID 59451645, compound

HRID 1874766Notes

Reaction equation

HRID 1874766 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([Cl:19])=[C:7]([O:9][C:10]2[CH:11]=[C:12]([CH:15]=[C:16]([Cl:18])[CH:17]=2)[C:13]#[N:14])[CH:8]=1.[CH3:20][C:21]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:22]=1[C:23](O)=[O:24].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>C(#N)C.CCOC(C)=O.CN(C=O)C>[Cl:19][C:6]1[CH:5]=[CH:4][C:3]([CH2:2][NH:1][C:23](=[O:24])[C:22]2[CH:26]=[CH:27][C:28]([O:30][CH3:31])=[CH:29][C:21]=2[CH3:20])=[CH:8][C:7]=1[O:9][C:10]1[CH:11]=[C:12]([C:13]#[N:14])[CH:15]=[C:16]([Cl:18])[CH:17]=1

Participants

9

Reactant 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 5972164-Methoxy-2-methylbenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 594514053-{[5-(Aminomethyl)-2-chlorophenyl]oxy}-5-chlorobenzonitrile

Product 1

HCID 59451645HCID 59451645, compoundYield 45.3%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-{[5-(Aminomethyl)-2-chlorophenyl]oxy}-5-chlorobenzonitrile (0.15 g, 0.51 mmol), 2-methyl-4-(methyloxy)benzoic acid (0.6 g, 0.25 mmol), HATU (0.21 g, 0.56 mmol) and DIPEA (0.11 mL, 0.60 mmol) were dissolved in acetonitrile (3 mL) and DMF (1 mL) then stirred overnight. EtOAc (25 mL) and saturated NaHCO3 (10 mL) were added. The layers were separated and the aqueous layer was extracted with EtOAc (2×10 mL). The organic extracts were combined, dried over Na2SO4, filtered and evaporated. Purification was accomplished by Reverse-Phase HPLC (water/acetonitrile with 0.1% TFA) to afford the title compound (0.05 g, 19%) as a white solid. 1H NMR (400 MHz, DMSO-d5): δ ppm 8.63 (s, 1H), 7.82 (d, 1H), 7.59 (d, 1H), 7.46 (dd, 1H), 7.39 (d, 1H), 7.26 (t, 2H), 7.16 (d, 1H), 6.73-6.78 (m, 2H), 4.38 (d, 2H), 3.73 (s, 3H), 2.25 (s, 3H). MS: m/z 441.0 (M+1).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with EtOAc (2×10 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customPurification

Sources & evidence

ORD record
ord-a887421640d04e7e866aba9c347fa0f4
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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