Acetic Acid → HCID 25119234, compound

HRID 1783475Notes

Reaction equation

HRID 1783475 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[N:11][N:12]([CH:14]2[CH2:18][NH:17][CH:16]([C:19]([N:21]3[CH2:26][CH2:25][N:24]([C:27]4[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=4[C:29]#[N:30])[CH2:23][CH2:22]3)=[O:20])[CH2:15]2)[N:13]=1.[CH:35](=O)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH2:35]([N:17]1[CH2:18][C@@H:14]([N:12]2[N:11]=[N:10][C:9]([C:3]3[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=3[F:1])=[N:13]2)[CH2:15][C@H:16]1[C:19]([N:21]1[CH2:22][CH2:23][N:24]([C:27]2[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=2[C:29]#[N:30])[CH2:25][CH2:26]1)=[O:20])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 66916032HCID 66916032, compound

Product 1

HCID 25119234HCID 25119234, compoundYield 2,069%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(4-{4-[5-(2,4-Difluoro-phenyl)-tetrazol-2-yl]-pyrrolidine-2-carbonyl}-piperazin-1-yl)-benzonitrile (0.136 g, 0.29 mmol), benzaldehyde (0.034 g, 0.32 mmol) and acetic acid (cat) was dissolved in DCM (20 ml) and the solution was stirred for 20 min. Then NaBH(OAc)3 (0.12 g, 0.58 mmol) was carefully added. The resulting mixture was warmed to r.t and stirred overnight. The solution was then washed with sat NaHCO3, brine, dried and concentrated to afford the title product as yellow oil (0.15 g, 6 mmol). MS m/e=555.4 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-911d1835086b4f06a416ec2bd8c09d3c
Source dataset
uspto-grants-2009_03
Patent number
US07501422B2

Reaction notes

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