Sulfuric Acid → HCID 24797452, compound

HRID 2261017Notes

Reaction equation

HRID 2261017 reaction equation
N[C:2]1[C:10]2[C:5](=[N:6][C:7]([CH:31]([CH3:33])[CH3:32])=[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]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)=[O:19])=[CH:13][CH:12]=2)[N:4]([CH3:34])[N:3]=1.S(=O)(=O)(O)O.N([O-])=O.[Na+]>>[CH:31]([C:7]1[N:6]=[C:5]2[N:4]([CH3:34])[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]([C:27]([F:28])([F:29])[F:30])[CH:22]=3)=[O:19])=[CH:15][CH:16]=2)[CH:8]=1)([CH3:33])[CH3:32]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 23668193Sodium NitriteHCID 59592670HCID 59592670, compound

Product 1

HCID 24797452HCID 24797452, compoundYield 12%

Procedure

In analogy to GP 6, reaction of 200 mg of 1-[4-(3-Amino-6-isopropyl-1-methyl-1H-pyrazolo[3,4-b]pyridin-4-yl)-phenyl]-3-(3-trifluoromethyl-phenyl)-urea (0.43 mmol, 1 eq.) with 67 μL concentrated sulphuric acid and 146 mg sodium nitrite (5 eq.) yielded 23 mg of the desired product (12% yield).

Sources & evidence

ORD record
ord-906b88520fd84a0db7871d583f4fd5a5
Source dataset
uspto-grants-2010_12
Patent number
US07846928B2

Reaction notes

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