Dichloromethane → 2-[3-(3-ethyl-1-methyl-2-oxo-azepan-3-yl)-phenoxy]-4-(3H-imidazol-4-ylmethyl)-benzonitrile hydrochloride

HRID 1594868Notes

Reaction equation

HRID 1594868 reaction equation
[CH2:1]([C:3]1([C:12]2[CH:13]=[C:14]([CH:49]=[CH:50][CH:51]=2)[O:15][C:16]2[CH:23]=[C:22]([CH2:24][C:25]3[N:26]=[CH:27][N:28](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:29]=3)[CH:21]=[CH:20][C:17]=2[C:18]#[N:19])[CH2:9][CH2:8][CH2:7][CH2:6][N:5]([CH3:10])[C:4]1=[O:11])[CH3:2].C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O.C(Cl)[Cl:67]>>[ClH:67].[CH2:1]([C:3]1([C:12]2[CH:13]=[C:14]([CH:49]=[CH:50][CH:51]=2)[O:15][C:16]2[CH:23]=[C:22]([CH2:24][C:25]3[NH:26][CH:27]=[N:28][CH:29]=3)[CH:21]=[CH:20][C:17]=2[C:18]#[N:19])[CH2:9][CH2:8][CH2:7][CH2:6][N:5]([CH3:10])[C:4]1=[O:11])[CH3:2]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 109085302-[3-(3-ethyl-1-methyl-2-oxo-azepan-3-yl)-phenoxy]-4-(1-trityl-1H-imidazol-4-ylmethyl)-benzonitrile

Product 1

HCID 217062752-[3-(3-ethyl-1-methyl-2-oxo-azepan-3-yl)-phenoxy]-4-(3H-imidazol-4-ylmethyl)-benzonitrile hydrochloride

Procedure

2-[3-(3-ethyl-1-methyl-2-oxo-azepan-3-yl)-phenoxy]-4-(1-trityl-1H-imidazol-4-ylmethyl)-benzonitrile (as described in Example 15, Step B) (0.074 g, 0.110 mmol) and triethylsilane (0.140 mL, 0.828 mmol) were stirred in CH2Cl2 (5 mL) and TFA (2.5 mL) for 1 h. The solution was concentrated in vacuo and purified using reverse phase chromatography (95/5-5/95 H2O/CH3CN with 0.1% TFA, flow=65 mL/min). The compound was converted to its free base using saturated NaHCO3 solution, extracted with CH2Cl2 (3×), dried (MgSO4), filtered and treated with 1N HCl ethereal solution to give the title compound.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. custompurified
  3. extractionextracted with CH2Cl2 (3×)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. additiontreated with 1N HCl ethereal solution

Sources & evidence

ORD record
ord-74aa193c95934926b68ca50ebbf7ff39
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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