HCID 58102975, compound → HCID 66851844, compound

HRID 1040249Notes

Reaction equation

HRID 1040249 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([C:14]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]4[N:27]([CH:28]5[CH2:30][CH2:29]5)[CH:26]=[N:25][N:24]=4)[CH:18]=3)=[O:15])[CH:9]=2)=[CH:4][CH:3]=1>C1(N)CC1>[CH:28]1([N:27]2[CH:26]=[N:25][N:24]=[C:23]2[C:19]2[CH:18]=[C:17]([NH:16][C:14]([C:10]3[CH:9]=[C:8]([C:5]4[CH:6]=[N:7][C:2]([NH:27][CH:28]5[CH2:30][CH2:29]5)=[CH:3][CH:4]=4)[CH:13]=[CH:12][N:11]=3)=[O:15])[CH:22]=[CH:21][CH:20]=2)[CH2:30][CH2:29]1

Participants

3

Reactant 1

HCID 58102975HCID 58102975, compound

Product 1

HCID 66851844HCID 66851844, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 69828CyclopropylamineSolvent

Conditions

Temperature
110 °C

Procedure

6-Chloro-N-(3-(4-cyclopropyl-4H-1,2,4-triazol-3-yl)phenyl)-3,4′-bipyridine-2′-carboxamide (60.0 mg, 0.144 mmol) was dissolved in cyclopropylamine (250 μL), and the mixture was heated to 110° C. for 2 days. The amine was removed under reduced pressure, and the residue was purified by reverse phase HPLC. The product (N-(3-(4-cyclopropyl-4H-1,2,4-triazol-3-yl)phenyl)-6-(cyclopropylamino)-3,4′-bipyridine-2′-carboxamide, 31.2 mg, 50% yield) was isolated as a white solid.

Workup

  1. customThe amine was removed under reduced pressure
  2. customthe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-60869ead08a74c58bcd0595a74f0e474
Source dataset
uspto-grants-2013_10
Patent number
US08552196B2

Reaction notes

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