Benzoyl chloride → 2-[(S)-1-(3-(benzoylamino)phenyl)ethylamino]-4-[benzimidazol-1-yl]pyrimidine

HRID 2300892Notes

Reaction equation

HRID 2300892 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C@@H:8]([NH:10][C:11]2[N:16]=[C:15]([N:17]3[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[N:19]=[CH:18]3)[CH:14]=[CH:13][N:12]=2)[CH3:9])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[C:33](Cl)(=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C(Cl)Cl>[C:33]([NH:1][C:2]1[CH:3]=[C:4]([C@@H:8]([NH:10][C:11]2[N:16]=[C:15]([N:17]3[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[N:19]=[CH:18]3)[CH:14]=[CH:13][N:12]=2)[CH3:9])[CH:5]=[CH:6][CH:7]=1)(=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 699621012-[(S)-1-(3-aminophenyl)ethylamino]-4-[benzimidazol-1-yl]pyrimidine

Product 1

HCID 599248922-[(S)-1-(3-(benzoylamino)phenyl)ethylamino]-4-[benzimidazol-1-yl]pyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[(S)-1-(3-aminophenyl)ethylamino]-4-[benzimidazol-1-yl]pyrimidine (10.0 mg) in CH2Cl2 (2 mL) was added triethylamine (13 μL) and benzoyl chloride (3.5 μL). The resulting solution was stirred at room temperature for 30 min. then the volatiles removed in vacuo. The residue was purified on silica gel (2%(2M NH3 in MeOH)/CH2Cl2) then HPLC (Zorbax Rx-SIL, 70:30 hexanes:ethanol) to yield 1.8 mg of the title compound. 1H NMR (500 MHz, CDCl3, partial): δ 8.41 (d, J=5.5 Hz, 1H); 7.87 (m, 2H); 7.82 (m, 2H); 7.76 (s, 1H); 7.58 (m, 2H); 7.51 (m, 2H); 7.41 (t, J=7.9 Hz, 1H); 6.80 (d, J=5.5 Hz, 1H); 1.67 (d, J=6.9 Hz, 3H).

Workup

  1. customthe volatiles removed in vacuo
  2. customThe residue was purified on silica gel (2%(2M NH3 in MeOH)/CH2Cl2)

Sources & evidence

ORD record
ord-6380b86829d844e4b51b5b4324323e90
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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