Sodium Bicarbonate → HCID 90017711, compound

HRID 1055004Notes

Reaction equation

[CH2:1]([C:3]1[C:4]([NH:10][NH:11][C:12](=O)[CH2:13][CH2:14][C:15]2[N:19]([CH3:20])[N:18]=[C:17]([N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)[N:16]=2)=[N:5][C:6]([CH3:9])=[N:7][CH:8]=1)[CH3:2].CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH2:1]([C:3]1[C:4]2[N:5]([C:12]([CH2:13][CH2:14][C:15]3[N:19]([CH3:20])[N:18]=[C:17]([N:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)[N:16]=3)=[N:11][N:10]=2)[C:6]([CH3:9])=[N:7][CH:8]=1)[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

N′-(5-Ethyl-2-methylpyrimidin-4-yl)-3-(1-methyl-3-(pyrrolidin-1-yl)-1H-1,2,4-triazol-5-yl)propanehydrazide (56.6 mg, 158 μmol) in tetrahydrofuran (4 ml) was added to Burgess reagent (155 mg, 632 μmol). The mixture was heated in a sealed tube at 80° C. for 1 h. Saturated sodium bicarbonate solution was added and extracted with dichloromethane. The organic layers were dried over sodium sulfate and concentrated to an oil to afford the desired product (69 mg) as a yellow solid which was used without further purification in the next step. MS: m/z=341.2 (M+H+)

Workup

extractionextracted with dichloromethane
dry with materialThe organic layers were dried over sodium sulfate
concentrationconcentrated to an oil

Sources & evidence

ORD record: ord-922df7ab2a5d4cf6bd9ed24684fec3b8
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394311B2

Reaction notes

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