Potassium Hydroxide → HCID 90415973, compound

HRID 869124Notes

Reaction equation

HRID 869124 reaction equation
[NH2:1][C:2]1[C:6]([C:7]([NH:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][C:15]=2[O:16][CH3:17])=[O:8])=[C:5]([NH2:18])[NH:4][N:3]=1.[CH2:19]([O:22][CH2:23][C:24](=O)[CH2:25][CH:26]1OCCO1)[CH:20]=[CH2:21].[OH-].[K+]>CCO>[CH2:19]([O:22][CH2:23][C:24]1[CH:25]=[CH:26][N:4]2[N:3]=[C:2]([NH2:1])[C:6]([C:7]([NH:9][C:10]3[CH:11]=[N:12][CH:13]=[CH:14][C:15]=3[O:16][CH3:17])=[O:8])=[C:5]2[N:18]=1)[CH:20]=[CH2:21]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 90410181HCID 90410181, compoundHCID 90418245HCID 90418245, compound

Product 1

HCID 90415973HCID 90415973, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3,5-Diamino-N-(4-methoxy-3-pyridyl)-1H-pyrazole-4-carboxamide 9 (250 mg, 1.007 mmol), 1-allyloxy-3-(1,3-dioxolan-2-yl)propan-2-one (187.5 mg, 1.007 mmol) and KOH (5.650 mg, 0.1007 mmol) were suspended in dry EtOH (5 mL) and stirred at RT for 2 hr. The light brown suspension was filtered and the collected solid was purified by column chromatography on silica (7.5% MeOH in DCM, ˜75 mL) to give the desired Compound I-O-55 as a light yellow solid (206.5 mg, 58% Yield). LC-MS (M+H)+ 355.2; 1H NMR (500 MHz, DMSO-d6) δ 10.19 (s, 1H), 9.52 (s, 1H), 8.95 (d, J=6.9 Hz, 1H), 8.21 (d, J=5.5 Hz, 1H), 7.16 (d, J=5.5 Hz, 1H), 7.09 (d, J=6.9 Hz, 1H), 6.62 (s, 2H), 6.01 (ddt, J=17.3, 10.6, 5.4 Hz, 1H), 5.37 (dq, J=17.3, 1.8 Hz, 1H), 5.24 (ddt, J=10.5, 2.0, 1.3 Hz, 1H), 4.71 (s, 2H), 4.18 (dt, J=5.4, 1.5 Hz, 2H), 4.03 (s, 3H).

Workup

  1. filtrationThe light brown suspension was filtered
  2. customthe collected solid was purified by column chromatography on silica (7.5% MeOH in DCM, ˜75 mL)

Sources & evidence

ORD record
ord-b6eb24f5eeda440fa666bdb816f78532
Source dataset
uspto-grants-2015_03
Patent number
US08969360B2

Reaction notes

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