Dimethylformamide → (R)-1-(7-bromo-3-(ethylamino)-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea

HRID 590815Notes

Reaction equation

HRID 590815 reaction equation
[CH2:1]([NH:3][C:4]1[C:8]2[CH:9]=[N:10][C:11]([NH:13][C:14]([NH:16][C@@H:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH3:18])=[O:15])=[CH:12][C:7]=2[NH:6][N:5]=1)[CH3:2].CN(C=O)C.C1C(=O)N([Br:37])C(=O)C1>C(#N)C>[Br:37][C:12]1[C:7]2[NH:6][N:5]=[C:4]([NH:3][CH2:1][CH3:2])[C:8]=2[CH:9]=[N:10][C:11]=1[NH:13][C:14]([NH:16][C@@H:17]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH3:18])=[O:15]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 67184N-bromobutanimideHCID 73504570(R)-1-(3-(ethylamino)-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea

Product 1

HCID 118272346(R)-1-(7-bromo-3-(ethylamino)-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(R)-1-(3-(Ethylamino)-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea (Example 2; 316 mg, 0.974 mmol) was dissolved in acetonitrile (10 mL) and DMF (2 mL) then NBS (225 mg, 1.266 mmol) was added. The reaction was stirred at room temperature overnight. The solvents were concentrated in vacuo and the residue was purified by flash chromatography (2-10% MeOH/DCM) to give (R)-1-(7-bromo-3-(ethylamino)-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea. MS ESI calc'd. for C12H19BrN6O [M+1]+ 403. found 403.

Workup

  1. concentrationThe solvents were concentrated in vacuo
  2. customthe residue was purified by flash chromatography (2-10% MeOH/DCM)

Sources & evidence

ORD record
ord-62c8bb4e96924fbf99af660f29507af2
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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