Diisopropylethylamine → HCID 71135220, compound

HRID 629871Notes

Reaction equation

HRID 629871 reaction equation
[CH3:1][C:2]([CH3:25])([CH3:24])[CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([C:13]3[CH:14]4[CH2:21][CH2:20][CH:17]([C:18]=3[CH3:19])[NH:16][CH2:15]4)=[CH:10][CH:11]=2)[N:6]([CH3:22])[C:5]1=[O:23].[O:26]1[CH:30]=[CH:29][C:28]([C:31](O)=[O:32])=[N:27]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>[CH3:1][C:2]([CH3:25])([CH3:24])[CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([C:13]3[CH:14]4[CH2:21][CH2:20][CH:17]([C:18]=3[CH3:19])[N:16]([C:31]([C:28]3[CH:29]=[CH:30][O:26][N:27]=3)=[O:32])[CH2:15]4)=[CH:10][CH:11]=2)[N:6]([CH3:22])[C:5]1=[O:23]

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 71135235HCID 71135235, compound

Product 1

HCID 71135220HCID 71135220, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(2,2-Dimethylpropyl)-3-methyl-5-(6-methyl-2-azabicyclo[2.2.2]oct-5-en-5-yl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (7-4, 8.6 mg, 0.03 mmol, 1.0 equiv), isoxazole-3-carboxylic acid (2-6, 4.3 mg, 0.04 mmol, 1.5 equiv), DIPEA (13 μL, 0.08 mmol, 3.0 equiv) and HATU (14.4 mg, 0.04 mmol, 1.5 equiv) were added to anhydrous acetonitrile (253 μL). After stirring for 10 min at room temperature, LCMS showed consumption of starting material. Purification by reverse-phase HPLC (10-100% CH3CN:0.1% TFA in H2O) provided 7-5 as a white solid. MS m/z (M+H): calculated=436.2343; observed=436.2351.

Workup

  1. customconsumption of starting material
  2. customPurification by reverse-phase HPLC (10-100% CH3CN:0.1% TFA in H2O)

Sources & evidence

ORD record
ord-f970936f33704130a41ed9ea05eab141
Source dataset
uspto-grants-2016_04
Patent number
US09315518B2

Reaction notes

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