Imidazole → HCID 67278441, compound

HRID 1696215Notes

Reaction equation

HRID 1696215 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:8][CH2:7][CH2:6][C@H:5]([NH:9][C:10]2[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][N:13]=[C:12]3[NH:21][CH:22]=[CH:23][C:11]=23)[CH2:4]1.N1C=CN=C1.Cl[Si:30]([CH:37]([CH3:39])[CH3:38])([CH:34]([CH3:36])[CH3:35])[CH:31]([CH3:33])[CH3:32].O>CN(C)C=O.CCOC(C)=O>[CH:31]([Si:30]([CH:37]([CH3:39])[CH3:38])([CH:34]([CH3:36])[CH3:35])[O:1][CH2:2][C@@H:3]1[CH2:8][CH2:7][CH2:6][C@H:5]([NH:9][C:10]2[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][N:13]=[C:12]3[NH:21][CH:22]=[CH:23][C:11]=23)[CH2:4]1)([CH3:33])[CH3:32]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 139400Triisopropylsilyl chlorideHCID 67277991HCID 67277991, compound

Product 1

HCID 67278441HCID 67278441, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 4-{[cis-3-(hydroxymethyl)cyclohexyl]amino}-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (125 mg) in N,N-dimethylformamide (1.25 ml) were added imidazole (40 mg) and chloro(triisopropyl)silane (125 μl). The mixture was stirred at ambient temperature for 18 hours. To the mixture were added water and EtOAc. The mixture was extracted with EtOAc and washed with saturated aqueous sodium hydrogencarbonate and brine. The extract was dried over MgSO4, filtrated and evaporated. The residue was purified by column chromatography on silica gel with chloroform:methanol=100:1-95:5 to give ethyl 4-{[cis-3-{[(triisopropylsilyl)oxy]methyl}cyclohexyl]amino}-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (170 mg) as a brown oil.

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. washwashed with saturated aqueous sodium hydrogencarbonate and brine
  3. dry with materialThe extract was dried over MgSO4
  4. filtrationfiltrated
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel with chloroform

Sources & evidence

ORD record
ord-e7e0a1d4886d4ac29ac3315a9525eaa1
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

Loading…