Benzylamine → N-(6-(benzylamino)-5-methylpyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide

HRID 39460Notes

Reaction equation

HRID 39460 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:10]1[N:15]=[C:14]([NH:16][C:17]([C:19]2([C:22]3[CH:32]=[CH:31][C:25]4[O:26][C:27]([F:30])([F:29])[O:28][C:24]=4[CH:23]=3)[CH2:21][CH2:20]2)=[O:18])[CH:13]=[CH:12][C:11]=1[CH3:33]>>[CH2:1]([NH:8][C:10]1[N:15]=[C:14]([NH:16][C:17]([C:19]2([C:22]3[CH:32]=[CH:31][C:25]4[O:26][C:27]([F:30])([F:29])[O:28][C:24]=4[CH:23]=3)[CH2:20][CH2:21]2)=[O:18])[CH:13]=[CH:12][C:11]=1[CH3:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 59165796N-(6-chloro-5-methylpyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropane-1-carboxamide

Product 1

HCID 57895128N-(6-(benzylamino)-5-methylpyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide

Procedure

To benzylamine (0.5 mL, 4.6 mmol) was added N-(6-chloro-5-methylpyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide (37 mg, 0.1 mmol) and the reaction mixture was irradiated in the microwave at 170° C. for 60 minutes. The crude product purified by reverse-phase preparative liquid chromatography utilizing a gradient of 0-99% acetonitrile in water containing 0.05% trifluoracetic acid to yield the pure product. ESI-MS m/z calc. 437.4. found 438.3 (M+1)+; retention time 1.83 minutes.

Workup

  1. customthe reaction mixture was irradiated in the microwave at 170° C. for 60 minutes
  2. customThe crude product purified by reverse-phase preparative liquid chromatography
  3. customto yield the pure product

Sources & evidence

ORD record
ord-bc0ab6f846984665a2722d8fc0b5b201
Source dataset
uspto-grants-2013_09
Patent number
US08524910B2

Reaction notes

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