Imidazole → HCID 66701989, compound

HRID 729655Notes

Reaction equation

HRID 729655 reaction equation
C(N(CC)C(C)C)(C)C.[NH2:10][C@@H:11]([CH2:13][OH:14])[CH3:12].Cl[C:16]1[N:21]=[C:20]([S:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[C:25]=2[F:31])[N:19]=[C:18]([NH2:32])[CH:17]=1.N1C=CN=C1.[Si:38](Cl)([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39]>CN1C(=O)CCC1.C1COCC1>[Si:38]([O:14][CH2:13][C@H:11]([NH:10][C:16]1[CH:17]=[C:18]([NH2:32])[N:19]=[C:20]([S:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[C:25]=2[F:31])[N:21]=1)[CH3:12])([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39]

Participants

8

Reactant 5

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 80308(R)-(-)-2-Amino-1-propanolHCID 81531DiisopropylethylamineHCID 85927987HCID 85927987, compound

Product 1

HCID 66701989HCID 66701989, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

N,N-Diisopropylethylamine (5.2 ml) was added to a solution of (R)-alaninol (2.56 ml) and the subtitle product of step ii) in NMP (35 ml) and stirred at 100° C. for 24 h and then 140° C. for 24 h. After cooling to ambient temperature imidazole (2.60 g) and a solution of tert-butyldimethylsilyl chloride (2.60 g) in THF (10 ml) were added and stirring maintained for 1 h. The volatiles were removed in vacuo and the residue was purified by column chromatography (1:1 Et2O/iso-hexane) to afford the subtitle compound as a yellow oil. Yield: 1.70 g.

Workup

  1. temperaturemaintained for 1 h
  2. customThe volatiles were removed in vacuo
  3. customthe residue was purified by column chromatography (1:1 Et2O/iso-hexane)

Sources & evidence

ORD record
ord-b6883046849f4547baa8100ea9c00517
Source dataset
uspto-grants-2009_09
Patent number
US07582644B2

Reaction notes

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