Imidazole → HCID 67497565, compound

HRID 1628263Notes

Reaction equation

HRID 1628263 reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][CH2:8][OH:9])[N:5]=[C:4]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH:16][CH3:17])[CH:11]=2)[CH:3]=1.N1C=CN=C1.[C:23]([Si:27](Cl)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([CH3:26])([CH3:25])[CH3:24]>CN(C1C=CN=CC=1)C.CN(C=O)C>[NH2:1][C:2]1[N:6]([CH2:7][CH2:8][O:9][Si:27]([C:23]([CH3:26])([CH3:25])[CH3:24])([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:5]=[C:4]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH:16][CH3:17])[CH:11]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 69620817HCID 69620817, compound2×

Product 1

HCID 67497565HCID 67497565, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

Starting material 2-(5-amino-3-(2-(methylamino)pyridin-4-yl)-1H-pyrazol-1-yl)ethanol 30.A was prepared analagously to example 23.1. To a flask with 30.A (306 mg, 1.3 mmol) was added DMAP (16 mg, 0.13 mmol), 1H-imidazole (268 mg, 3.9 mmol). Then DMF 1.5 mL was added, followed by tert-butylchlorodiphenylsilane (505 mg, 1.8 mmol). The reaction was stirred overnight. Standard aqueous workup and silica gel chromatography afforded 618 mg (100%) 30.B.

Workup

  1. customwas prepared analagously to example 23.1

Sources & evidence

ORD record
ord-406d0bbb849644af9d60ca3ded7af2f6
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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