Diisopropylethylamine → HCID 71136617, compound

HRID 629864Notes

Reaction equation

HRID 629864 reaction equation
[CH:1]12[CH2:24][CH2:23][CH:4]([CH:5]([C:7]3[N:12]=[C:11]4[N:13]([CH3:22])[C:14](=[O:21])[N:15]([CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:10]4=[CH:9][CH:8]=3)[CH2:6]1)[CH2:3][NH:2]2.[O:25]1[CH:29]=[CH:28][C:27]([C:30](O)=[O:31])=[N:26]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>O1CCOCC1>[CH3:18][C:17]([CH3:19])([CH3:20])[CH2:16][N:15]1[C:10]2[C:11](=[N:12][C:7]([CH:5]3[CH2:6][CH:1]4[CH2:24][CH2:23][CH:4]3[CH2:3][N:2]4[C:30]([C:27]3[CH:28]=[CH:29][O:25][N:26]=3)=[O:31])=[CH:8][CH:9]=2)[N:13]([CH3:22])[C:14]1=[O:21]

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 112864533-Isoxazolecarboxylic acidHCID 71136621HCID 71136621, compound

Product 1

HCID 71136617HCID 71136617, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5-(2-Azabicyclo[2.2.2]oct-5-yl)-1-(2,2-dimethylpropyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (5-1, 30.2 mg, 0.09 mmol, 1.0 equiv), isoxazole-3-carboxylic acid (2-6, 15.6 mg, 0.14 mmol, 1.5 equiv), DIPEA (48 μL, 0.28 mmol, 3.0 equiv) and HATU (52.4 mg, 0.14 mmol, 1.5 equiv) were added to anhydrous 1,4-dioxane (0.92 mL). After stirring for 10 min at room temperature, LCMS showed consumption of starting material. Purification by reverse-phase HPLC (20-100% CH3CN:0.1% TFA in H2O) provided 5-2 as a white solid. MS m/z (M+H): calculated=424.2343; observed=424.2345.

Workup

  1. customconsumption of starting material
  2. customPurification by reverse-phase HPLC (20-100% CH3CN:0.1% TFA in H2O)

Sources & evidence

ORD record
ord-2346a48680e74e6993f4e95e35047254
Source dataset
uspto-grants-2016_04
Patent number
US09315518B2

Reaction notes

Loading…