1-Methylpiperazine → HCID 24865996, compound

HRID 506164Notes

Reaction equation

HRID 506164 reaction equation
[CH:1]([C:3]1[S:7][C:6]([C:8]2[CH:9]=[C:10]([C:14]3[CH:15]=[N:16][CH:17]=[C:18]([C:21]=3[NH:22][C:23]3[CH:24]=[C:25]4[C:29](=[CH:30][CH:31]=3)[NH:28][CH:27]=[CH:26]4)[C:19]#[N:20])[CH:11]=[CH:12][CH:13]=2)=[CH:5][CH:4]=1)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[CH3:46][N:47]1[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]1>C(Cl)Cl.CN1C(=O)CCC1>[NH:28]1[C:29]2[C:25](=[CH:24][C:23]([NH:22][C:21]3[C:18]([C:19]#[N:20])=[CH:17][N:16]=[CH:15][C:14]=3[C:10]3[CH:11]=[CH:12][CH:13]=[C:8]([C:6]4[S:7][C:3]([CH2:1][N:50]5[CH2:51][CH2:52][N:47]([CH3:46])[CH2:48][CH2:49]5)=[CH:4][CH:5]=4)[CH:9]=3)=[CH:31][CH:30]=2)[CH:26]=[CH:27]1

Participants

6

Reactant 3

HCID 531671-MethylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 24864896HCID 24864896, compound

Product 1

HCID 24865996HCID 24865996, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To 5-[3-(5-formyl-2-thienyl)phenyl]-4-(1H-indol-5-ylamino)nicotinonitrile 150 (100 mg, 0.238 mmol) in CH2Cl2 (5 mL) and NMP (0.5 mL), cooled with ice-water bath, was added Na(OAc)3BH (264 mg, 1.2 mmol) and N-methylpiperazine (133 μL, 1.2 mmol). The resulting mixture was stirred at r.t. overnight and partitioned between CH2Cl2 and aq. NaHCO3. The combined organics were dried over Na2SO4, concentrated and purified by preparative TLC eluting with 10% MeOH/CH2Cl2 to give 63 mg (53% yield) of the title compound as a light yellow solid. MS: 505.2 (M+H); melting range: 120-123° C.

Workup

  1. custompartitioned between CH2Cl2 and aq. NaHCO3
  2. dry with materialThe combined organics were dried over Na2SO4
  3. concentrationconcentrated
  4. custompurified by preparative TLC
  5. washeluting with 10% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-048fa6b3170549bf82813e0013222715
Source dataset
uspto-grants-2010_08
Patent number
US07781591B2

Reaction notes

Loading…