Diisopropylethylamine → (5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-[3-(tert-butyl-dimethyl-silanyloxymethyl)-4-morpholin-4-yl-phenyl]-amine

HRID 1924999Notes

Reaction equation

HRID 1924999 reaction equation
[Br:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[C:5](Br)=[N:4][CH:3]=1.[C:12]([SiH2:16][O:17][C:18]([CH3:33])([CH3:32])[C:19]1[CH:20]=[C:21]([NH2:31])[CH:22]=[CH:23][C:24]=1[N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1)([CH3:15])([CH3:14])[CH3:13].C(N(CC)C(C)C)(C)C>C(O)(C)C>[Br:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[C:5]([NH:31][C:21]2[CH:22]=[CH:23][C:24]([N:25]3[CH2:26][CH2:27][O:28][CH2:29][CH2:30]3)=[C:19]([C:18]([CH3:33])([CH3:32])[O:17][SiH2:16][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:20]=2)=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 534859495,8-Dibromoimidazo[1,2-a]pyrazineHCID 1373286683-(Tert-butyl-dimethyl-silanyloxymethyl)-4-morpholin-4-yl-phenylamine

Product 1

HCID 131728706(5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-[3-(tert-butyl-dimethyl-silanyloxymethyl)-4-morpholin-4-yl-phenyl]-amineYield 21.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

In the same way as described in the general procedure for amine displacement using 5,8-dibromo-imidazo[1,2-a]pyrazine (0.534 g, 1.94 mmol), 3-(tert-butyl-dimethyl-silanyloxymethyl)-4-morpholin-4-yl-phenylamine (0.751 g, 2.33 mmol), N,N-diisopropyethylamine (0.31 mL, 1.8 mmol) and iso-propanol (10 mL). Purification by silica gel column chromatography eluting with 7:3 petroleum ether:ethyl acetate followed by trituration with diethyl ether affords the title compound (0.216 g, 17%).

Workup

  1. customPurification by silica gel column chromatography
  2. washeluting with 7:3 petroleum ether

Sources & evidence

ORD record
ord-283a6f5cd1ab43f385b62b2bf90a5393
Source dataset
uspto-grants-2012_05
Patent number
US08178530B2

Reaction notes

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