Acetic Acid → HCID 86625267, compound

HRID 1783471Notes

Reaction equation

HRID 1783471 reaction equation
[C:1]1([C:7]2[N:8]=[N:9][N:10]([CH:12]3[CH2:16][NH:15][CH:14]([C:17]([N:19]4[CH2:24][CH2:23][N:22]([C:25]5[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=5[C:27]#[N:28])[CH2:21][CH2:20]4)=[O:18])[CH2:13]3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:33](=O)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH2:33]([N:15]1[CH2:16][CH:12]([N:10]2[N:9]=[N:8][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[N:11]2)[CH2:13][CH:14]1[C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=2[C:27]#[N:28])[CH2:21][CH2:20]1)=[O:18])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 66915931HCID 66915931, compound

Product 1

HCID 86625267HCID 86625267, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(4-{4-[5-(Phenyl)-tetrazol-2-yl]-pyrrolidine-2-carbonyl}-piperazin-1-yl)-benzonitrile (2), benzaldehyde and acetic acid (cat) is dissolved in DCM and the solution is stirred for 20 min. Then NaBH(OAc)3 is added. The resulting mixture is warmed to r.t and stirred overnight. The solution is then washed with sat NaHCO3, brine, dried and concentrated to afford 2-(4-{1-Benzyl-4-[5-(phenyl)-tetrazol-2-yl]-pyrrolidine-2-carbonyl}-piperazin-1-yl)-benzonitrile (I).

Workup

  1. temperatureThe resulting mixture is warmed
  2. stirringstirred overnight
  3. washThe solution is then washed with sat NaHCO3, brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ea3e139e0a46420c876caf56eeffaa82
Source dataset
uspto-grants-2009_03
Patent number
US07501422B2

Reaction notes

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