Methanol → HCID 178490273, compound

HRID 2110641Notes

Reaction equation

HRID 2110641 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH:11][C:12]2[CH:17]=[C:16]([C:18]3[CH:45]=[CH:44][C:21]4[N:22](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[CH:23]=[N:24][C:20]=4[CH:19]=3)[N:15]=[C:14]([O:46][CH3:47])[N:13]=2)=[CH:5][CH:4]=1.FC(F)(F)C(O)=O.O.CO>C(Cl)Cl>[NH:22]1[C:21]2[CH:44]=[CH:45][C:18]([C:16]3[N:15]=[C:14]([O:46][CH3:47])[N:13]=[C:12]([NH:11][CH2:10][CH2:9][C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=4)[CH:17]=3)=[CH:19][C:20]=2[N:24]=[CH:23]1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 6422Trifluoroacetic acidHCID 57636034HCID 57636034, compound2×

Product 1

HCID 178490273HCID 178490273, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of [2-(4-methoxy-phenyl)-ethyl]-[2-methoxy-6-(1-trityl-1H-benzoimidazol-5-yl)-pyrimidin-4-yl]-amine [300 mg, 0.485 mmol, Intermediate (28)], DCM (5 mL), trifluoroacetic acid (2 mL) and water (5%) is stirred at ambient temperature. The reaction mixture is concentrated by rotary evaporator to remove the solvent. The residue is taken up in saturated sodium bicarbonate solution and this solution is extracted with ethyl acetate. The extract is dried over magnesium sulfate, filtered and concentrated to provide a solid, which is subjected to flash column chromatography on silica gel eluting with 5% MeOH in DCM to afford [6-(1H-benzoimidazol-5-yl)-2-methoxy-pyrimidin-4-yl]-[2-(4-methoxy-phenyl)-ethyl]-amine [90 mg, 49%, Example 14(a)]. LCMS: RT=4.73 minutes, MS: 376 (M+H). IC50=2.7 nM

Workup

  1. concentrationThe reaction mixture is concentrated by rotary evaporator
  2. customto remove the solvent
  3. extractionthis solution is extracted with ethyl acetate
  4. dry with materialThe extract is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto provide a solid, which

Sources & evidence

ORD record
ord-a0c0592acb884b09856838171696d663
Source dataset
uspto-grants-2009_04
Patent number
US07517889B2

Reaction notes

Loading…