Acetic Acid → HCID 178420281, compound

HRID 45975Notes

Reaction equation

HRID 45975 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]=O)=[CH:9][C:4]=2[NH:3][CH:2]=1.[C:12]1([CH2:18][CH2:19][NH2:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O>>[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][NH:20][CH2:19][CH2:18][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 1001PhenethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 100120381H-1,3-benzodiazole-5-carbaldehyde

Product 1

HCID 178420281HCID 178420281, compound

Procedure

The compound was synthesized starting from benzimidazol-5-carbaldehyde (146 mg; 1 mmol; 1 eq.), phenylethylamine (0.126 ml; 1 mmol; 1 eq.); NaBH(AcO)3 (318 mg; 1.5 mmol; 1.5 eq.) and AcOH (0.095 ml; 1.5 mmol; 1.5 eq.) as described above. Yield: 0.040 g (16%); MS m/z: 252.2 [M+H]+; 1H-NMR (400 MHz, DMSO d6): δ 3.30 (br s, 4H); 3.81 (s, 2H); 7.12-7.27 (m, 9H); 8.13-8.14 (m, 1H); 12.30 (br s, 1H); HPLC (METHOD [A]): rt doublepeak 6.77/6.60 min (93.7%)

Workup

  1. customThe compound was synthesized
  2. customrt
  3. custom6.60 min (93.7%)

Sources & evidence

ORD record
ord-92edcecd56f844f9ad978b87ef4c95a7
Source dataset
uspto-grants-2013_09
Patent number
US08541596B2

Reaction notes

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