HCID 59924696, compound → HCID 59924927, compound

HRID 2300821Notes

Reaction equation

HRID 2300821 reaction equation
[CH3:1][Mg]Br.[C:4]1([C@@H:10]([NH:12][C:13]2[N:18]=[C:17]([N:19]3[C:23]4[CH:24]=[CH:25][C:26]([C:28](N(C)OC)=[O:29])=[CH:27][C:22]=4[N:21]=[CH:20]3)[CH:16]=[CH:15][N:14]=2)[CH3:11])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(Cl)Cl>[C:4]1([C@@H:10]([NH:12][C:13]2[N:18]=[C:17]([N:19]3[C:23]4[CH:24]=[CH:25][C:26]([C:28]([CH3:1])=[O:29])=[CH:27][C:22]=4[N:21]=[CH:20]3)[CH:16]=[CH:15][N:14]=2)[CH3:11])[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 59924696HCID 59924696, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 59924927HCID 59924927, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of methylmagnesium bromide (980 μL, 1.4 M, 13.8 mmol) in CH2Cl2 (0.5 mL) at 0° C. was added 2-[(S)-1-phenylethylamino]-4-[5-(N-methyl-N-methoxyaminocarbonyl)-benzimidazol-1-yl]pyrimidine (55.4 mg, 0.138 mmol) in CH2Cl2 (1.0 mL) slowly. The reaction mixture was warmed to room temperature slowly and continued stirring for 5 h. The reaction mixture was quenched with saturated aqueous NH4Cl then extracted with CH2Cl2. The combined extracts were washed with brine and dried over Na2SO4. The crude material was purified by preparative thin layer chromatography eluting with 3% MeOH/CH2Cl2 to obtain 38 mg of the title compound. Partial 1H NMR (500 MHz, CDCl3): δ 8.5 (br s, 1H); 8.4 (s, 1H); 8.38 (d, J=5.5 Hz, 1H); 7.93 (br s, 1H); 7.79 (br s, 1H); 7.44-7.28 (m, 5H); 6.74 (d, J=5.2 Hz, 1H); 5.17 (br s, 1H); 2.68 (s, 3H); 1.63 (d, J=6.8 Hz, 3H). Mass spectrum 358.2 (CI, M+1).

Workup

  1. customThe reaction mixture was quenched with saturated aqueous NH4Cl
  2. extractionthen extracted with CH2Cl2
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. customThe crude material was purified by preparative thin layer chromatography
  6. washeluting with 3% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-c2e95926c5264c35a5356e86a6383a81
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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