Sulfuric Acid → HCID 24856719, compound

HRID 2261015Notes

Reaction equation

HRID 2261015 reaction equation
N[C:2]1[C:10]2[C:5](=[N:6][C:7]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:8][C:9]=2[C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][CH3:28])[CH:22]=3)=[O:19])=[CH:13][CH:12]=2)[NH:4][N:3]=1.S(=O)(=O)(O)O.N([O-])=O.[Na+]>>[C:29]([C:7]1[N:6]=[C:5]2[NH:4][N:3]=[CH:2][C:10]2=[C:9]([C:11]2[CH:12]=[CH:13][C:14]([NH:17][C:18]([NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][CH3:28])[CH:22]=3)=[O:19])=[CH:15][CH:16]=2)[CH:8]=1)([CH3:32])([CH3:31])[CH3:30]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 23668193Sodium NitriteHCID 178436417HCID 178436417, compound

Product 1

HCID 24856719HCID 24856719, compoundYield 42.9%

Procedure

In analogy to GP 6, reaction of 95.6 mg of 1-[4-(3-amino-6-tert-butyl-1H-pyrazolo-[3,4-b]pyridin-4-yl)-phenyl]-3-(3-ethyl-phenyl)-urea (0.22 mmol, 1 eq.) with 35 μL concentrated sulphuric acid and 38 mg sodium nitrite (2.5 eq.) yielded 39 mg of the desired product (42% yield).

Sources & evidence

ORD record
ord-c44122838cae4ed3bc412130b040610e
Source dataset
uspto-grants-2010_12
Patent number
US07846928B2

Reaction notes

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