Sulfuric Acid → HCID 24797379, compound

HRID 2261019Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1([C:9]2[N:14]=[C:13]3[N:15]([CH3:19])[N:16]=[C:17](N)[C:12]3=[C:11]([C:20]3[CH:25]=[CH:24][C:23]([NH:26][C:27]([NH:29][C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:39])([F:38])[F:37])[CH:31]=4)=[O:28])=[CH:22][CH:21]=3)[CH:10]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].S(=O)(=O)(O)O.N([O-])=O.[Na+]>>[CH2:1]([O:3][C:4]([C:6]1([C:9]2[N:14]=[C:13]3[N:15]([CH3:19])[N:16]=[CH:17][C:12]3=[C:11]([C:20]3[CH:21]=[CH:22][C:23]([NH:26][C:27]([NH:29][C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:39])([F:38])[F:37])[CH:31]=4)=[O:28])=[CH:24][CH:25]=3)[CH:10]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

Reactant 3

HCID 1118Sulfuric Acid

HCID 23668193Sodium Nitrite

HCID 59550634HCID 59550634, compound

Product 1

HCID 24797379HCID 24797379, compoundYield 48%

Procedure

In analogy to GP 6, reaction of 210 mg of 1-(3-Amino-1-methyl-4-{4-[3-(3-trifluoromethyl-phenyl)-ureido]-phenyl}-1H-pyrazolo[3,4-b]pyridin-6-yl)-cyclopropanecarboxylic acid ethyl ester (0.39 mmol, 1 eq.) with 31 μL concentrated sulphuric acid and 64.6 mg sodium nitrite (0.94 mmol, 2.4 eq.) yielded 97 mg of the desired product (48% yield).

Sources & evidence

ORD record: ord-f75e7063f3e944f0b3c9f12e88d24007
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07846928B2

Reaction notes

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