Water → HCID 90407317, compound

HRID 2277554Notes

Reaction equation

HRID 2277554 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][N:9]1[C:13]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[C:12]([C:21]2[CH:26]=[C:25]([C:27]3[N:28]=[N:29][NH:30][N:31]=3)[CH:24]=[CH:23][N:22]=2)[N:11]=[CH:10]1.Br[CH2:33][O:34][C:35](=[O:37])[CH3:36].CC([O-])(C)C.[K+].O>CN(C=O)C>[C:35]([O:34][CH2:33][N:29]1[N:30]=[N:31][C:27]([C:25]2[CH:24]=[CH:23][N:22]=[C:21]([C:12]3[N:11]=[CH:10][N:9]([CH2:8][C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[Cl:1])[C:13]=3[C:14]3[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=3)[CH:26]=2)=[N:28]1)(=[O:37])[CH3:36]

Participants

6

Reactant 4

HCID 962WaterHCID 68536Bromomethyl acetateHCID 23665647Potassium tert-butoxideHCID 90407363HCID 90407363, compound

Product 1

HCID 90407317HCID 90407317, compoundYield 8.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[1-[(2-chlorophenyl)methyl]-5-(4-fluorophenyl)imidazol-4-yl]-4-(2H-tetrazol-5-yl)pyridine (50 mg, 0.12 mmol, Example 137) in DMF (5 mL) was added acetic acid bromomethyl ester (20 mg, 0.12 mmol), t-BuOK (27 mg, 0.24 mmol) and KI (40 mg, 0.24 mmol) at 0° C., then the mixture was stirred for 72 hr at rt, H2O was added, extracted with EA, dried, concentrated and purified by HPLC to give the title compound (5 mg, 8.6%). 1H NMR (300 MHz, CD3OD): δ 2.13 (3H, s), 5.38 (2H, s), 6.55 (2H, s), 6.97-6.98 (1H, m), 7.23-7.49 (7H, m), 7.85 (1H, s), 8.10 (1H, d, J=6.0 Hz), 8.28 (1H, m), 8.64 (1H, m). [M+H] Calc'd for C25H19ClFN7O2, 504. Found, 504.

Workup

  1. extractionextracted with EA
  2. customdried
  3. concentrationconcentrated
  4. custompurified by HPLC

Sources & evidence

ORD record
ord-de754228f0f6412593819a71d26a5670
Source dataset
uspto-grants-2015_09
Patent number
US09133166B2

Reaction notes

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