Acetonitrile → HCID 68512093, compound

HRID 2241270Notes

Reaction equation

HRID 2241270 reaction equation
[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][N:8]2[C:12]3=[N:13][CH:14]=[CH:15][C:16]([O:17][C:18]4[CH:23]=[CH:22][C:21](N)=[CH:20][C:19]=4[F:25])=[C:11]3[C:10]([I:26])=[N:9]2)=[CH:5][CH:4]=1.[F:29][C:30]1[CH:35]=[CH:34][C:33]([NH:36][C:37]([C:39]2([C:42](F)=[O:43])[CH2:41][CH2:40]2)=[O:38])=[CH:32][CH:31]=1.C(#[N:47])C>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:12]3=[N:13][CH:14]=[CH:15][C:16]([O:17][C:18]4[CH:23]=[CH:22][C:21]([N:36]([C:33]5[CH:34]=[CH:35][C:30]([F:29])=[CH:31][CH:32]=5)[C:37]([C:39]5([C:42]([NH2:47])=[O:43])[CH2:41][CH2:40]5)=[O:38])=[CH:20][C:19]=4[F:25])=[C:11]3[C:10]([I:26])=[N:9]2)=[CH:27][CH:28]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 672210033-Fluoro-4-((3-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)oxy)anilineHCID 866146491-((4-Fluorophenyl)carbamoyl)cyclopropanecarbonyl fluoride

Product 1

HCID 68512093HCID 68512093, compoundYield 75%

Procedure

4-(1-(4-Methoxybenzyl)-3-iodo-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorobenzenamine (0.490 g, 1.0 mmol, prepared according to Example 7, Step B) and acetonitrile (5 mL) were heated with 1-((4-fluorophenyl)carbamoyl)-cyclopropanecarbonyl fluoride (0.450 g, 2.00 mmol, prepared according to Example 6, Step A) at 100° C. in a sealed vessel for 4 hours. The suspension was allowed to cool to ambient temperature, and then in an ice bath for 15 minutes. The solid was filtered to provide pure desired product (0.52 g, 75%) by LRMS (APCI−): 100% purity, 220 nm, m/z 694 (M−1) detected.

Workup

  1. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-f62c691418bf4e9fbb8cb41c928a3a32
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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