Diisopropylethylamine → HCID 71136787, compound

HRID 629918Notes

Reaction equation

HRID 629918 reaction equation
[NH2:1][CH2:2][CH:3]1[CH:5]([CH3:6])[CH:4]1[C:7]1[N:12]=[C:11]2[N:13]([CH3:22])[C:14](=[O:21])[N:15]([CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:10]2=[CH:9][CH:8]=1.[O:23]1[CH:27]=[CH:26][C:25]([C:28](O)=[O:29])=[N:24]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>C(#N)C>[CH3:19][C:17]([CH3:18])([CH3:20])[CH2:16][N:15]1[C:10]2[C:11](=[N:12][C:7]([CH:4]3[CH:5]([CH3:6])[CH:3]3[CH2:2][NH:1][C:28]([C:25]3[CH:26]=[CH:27][O:23][N:24]=3)=[O:29])=[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 71136775HCID 71136775, compound

Product 1

HCID 71136787HCID 71136787, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-[2-(Aminomethyl)-3-methylcyclopropyl]-1-(2,2-dimethylpropyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (35-2, 35 mg, 0.11 mmol, 1.0 equiv), isoxazole-3-carboxylic acid (2-6, 14.3 mg, 0.12 mmol, 1.5 equiv), DIPEA (0.040 mL, 0.23 mmol, 2.0 equiv) and HATU (48.4 mg, 0.12 mmol, 1.1 equiv) were added to anhydrous acetonitrile (1 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 35-3 as a white solid. MS m/z (M+H): calculated=398.2188; observed=398.2195. 1H NMR δ (ppm)(CHCl3-d): 8.47 (1H, d, J=1.68 Hz), 7.04 (1H, d, J=7.90 Hz), 6.96 (1H, s), 6.83 (1H, d, J=1.67 Hz), 6.81 (1H, d, J=7.90 Hz), 3.76-3.65 (1H, m), 3.61 (2H, s), 3.60-3.52 (1H, m), 3.43 (3H, s), 1.82 (1H, dd, J=7.68, 3.43 Hz), 1.70-1.65 (1H, m), 1.64 (1H, dd, J=7.82, 0.02 Hz), 1.30 (3H, d, J=6.23 Hz), 1.02 (9H, s).

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-5840f18f0bcc4f1597c5a53d30f61574
Source dataset
uspto-grants-2016_04
Patent number
US09315518B2

Reaction notes

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