Chlorotrimethylsilane → (E)-tert-Butyl 4-(5-(8-morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-5-yl)pyridin-2-yl)piperazine-1-carboxylate

HRID 1772630Notes

Reaction equation

HRID 1772630 reaction equation
[CH:1]([C:3]1[N:4]=[C:5]2[C:10]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[N:9][CH:8]=[C:7]([C:17]3[CH:18]=[CH:19][C:20]([N:23]4[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]4)=[N:21][CH:22]=3)[N:6]2[CH:36]=1)=O.[CH3:37][C:38]1[CH:47]=[CH:46][C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[N:39]=1.Cl[Si](C)(C)C.C([O-])(O)=O.[Na+]>CN(C=O)C.O>[O:14]1[CH2:15][CH2:16][N:11]([C:10]2[C:5]3[N:6]([CH:36]=[C:3](/[CH:1]=[CH:37]/[C:38]4[CH:47]=[CH:46][C:45]5[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=5)[N:39]=4)[N:4]=3)[C:7]([C:17]3[CH:18]=[CH:19][C:20]([N:23]4[CH2:24][CH2:25][N:26]([C:29]([O:31][C:32]([CH3:33])([CH3:34])[CH3:35])=[O:30])[CH2:27][CH2:28]4)=[N:21][CH:22]=3)=[CH:8][N:9]=2)[CH2:12][CH2:13]1

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 70602-MethylquinolineHCID 516892Sodium BicarbonateHCID 117733760tert-Butyl 4-(5-(2-formyl-8-morpholinoimidazo[1,2-a]pyrazin-5-yl)pyridin-2-yl)piperazine-1-carboxylate

Product 1

HCID 86346129(E)-tert-Butyl 4-(5-(8-morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-5-yl)pyridin-2-yl)piperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of compound 19a (50.0 mg, 0.101 mmol) in DMF (3 mL) was added 2-methylquinoline (13.2 μL, 0.101 mmol) and chlorotrimethylsilane (38.6 μL, 0.304 mmol). The reaction mixture was stirred in a 10 mL sealed tube for 2 h at 80° C. After cooling to rt, the reaction mixture was poured into water (20 mL). The mixture was adjusted to basic using saturated NaHCO3 solution, and was extracted with DCM (2×20 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated. Compound 19b was obtained as a yellow solid (40.0 mg, 64% yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C35H38N8O3: 619.3 (M+H). found: 619.3.

Workup

  1. customsealed tube for 2 h at 80° C
  2. extractionwas extracted with DCM (2×20 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ea31693a96ca4d959b3be73d515c641d
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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