Potassium Carbonate → HCID 178503177, compound

HRID 45966Notes

Reaction equation

HRID 45966 reaction equation
[CH:1]1([CH2:7][NH:8][C:9]2[CH:17]=[CH:16][C:12]3[N:13]=[CH:14][NH:15][C:11]=3[CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:18][S:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=1.C([O-])([O-])=O.[K+].[K+]>>[CH3:18][S:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][N:8]([CH2:7][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[C:9]2[CH:17]=[CH:16][C:12]3[NH:13][CH:14]=[N:15][C:11]=3[CH:10]=2)=[CH:22][CH:21]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 113679304-(Methylthio)benzyl bromideHCID 67445021N-cyclohexylmethyl-benzimidazol-5-amine

Product 1

HCID 178503177HCID 178503177, compound

Procedure

The compound was synthesized starting from N-cyclohexylmethyl-benzimidazol-5-amine (115 mg; 0.5 mmol; 1 eq.), 4-methylthiobenzylbromide (120 mg; 0.55 mmol; 1.1 eq.) and K2CO3 (76 mg; 0.55 mmol; 1.1 eq.) according to method 6; Yield: 0.068 g (37.3%); MS m/z: 366.4 [M+H]+; 1H-NMR (400 MHz, DMSO d6): δ 0.90-1.00 (m, 2H); 1.13-1.23 (m, 3H); 1.61-1.76 (m, 6H); 2.41 (s, 3H); 3.24 (d, 2H, 3J=6.6 Hz); 4.52 (s, 2H); 6.67-6.69 (m, 2H); 7.12-7.18 (m, 4H); 7.32-7.34 (m, 1H); 7.89 (s, 1H); 11.84 (br s, 1H); HPLC (METHOD [A]): rt 18.51 min (97.8%)

Workup

  1. customThe compound was synthesized
  2. customrt 18.51 min (97.8%)

Sources & evidence

ORD record
ord-68d015eb5ef74608a881d57f408d8a33
Source dataset
uspto-grants-2013_09
Patent number
US08541596B2

Reaction notes

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