1-Methylpiperazine → HCID 70114360, compound

HRID 85084Notes

Reaction equation

HRID 85084 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[C:18]4[C:13](=[N:14][CH:15]=[C:16]([C:19]5[CH:26]=[CH:25][C:22](C=O)=[C:21]([O:27][CH3:28])[CH:20]=5)[CH:17]=4)[N:12](S(C4C=CC(C)=CC=4)(=O)=O)[CH:11]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[CH3:39][N:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1.[C:46](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[C:18]4[C:13](=[N:14][CH:15]=[C:16]([C:19]5[CH:26]=[CH:25][C:22]([CH2:39][N:40]6[CH2:45][CH2:44][N:43]([CH3:46])[CH2:42][CH2:41]6)=[C:21]([O:27][CH3:28])[CH:20]=5)[CH:17]=4)[NH:12][CH:11]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 86691663HCID 86691663, compound

Product 1

HCID 70114360HCID 70114360, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[3-(1H-Indol-5-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-methoxy-benzaldehyde (0.066 g, 0.128 mmol) in CH2Cl2 (3 mL) was added 1-methylpiperazine (22 mL, 0.19 mmol) and sodium triacetoxyborohydride (81 mg, 0.38 mmol). The reaction mixture was stirred for 1 hr at room temperature, after which it was partitioned between CH2Cl2 and 1 M NaOH. The organic layer was separated, dried over MgSO4, and concentrated in vacuo. The residue was dissolved in 3:2 MeOH:acetone (5 mL), and 2 M NaOH (1.5 mL) was added. The resulting mixture was stirred at 65° C. for 30 min, after which it was partitioned between EtOAc and 1 M NaOH. The organic layer was separated, dried over MgSO4, filtered, and stripped to provide a residue that was subjected to preparatory HPLC to yield 3-(1H-Indol-5-yl)-5-[3-methoxy-4-(4-methyl-piperazin-1-ylmethyl)-phenyl]-1H-pyrrolo[2,3-b]pyridine (0.037 g, 63% yield). 1H NMR (CDCl3, 400 MHz): δ 11.81 (s, 1H), 11.06 (s, 1H), 8.55 (d, J=2.1 Hz, 1H), 8.40 (d, J=2.4 Hz, 1H), 7.88 (d, J=1.6 Hz, 1H), 7.74 (d, J=1.6 Hz, 1H), 7.46 (s, 2H), 7.37 (dd, J=6.4 Hz, 1H), 7.35 (d, J=6.4 Hz, 1H), 7.26 (dd, J=1.8, 6.4 Hz, 2H)), 6.46 (s, 1H), 3.86 (d, J=1.2 Hz, 2H), 3.32 (s, 3H), 2.49-42 (m, 8H), 2.13 (s, 3H); MS ESI (m/z) 452 (M+1)+, calc. 451.56.

Workup

  1. customafter which it was partitioned between CH2Cl2 and 1 M NaOH
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in 3:2 MeOH
  6. additionacetone (5 mL), and 2 M NaOH (1.5 mL) was added
  7. stirringThe resulting mixture was stirred at 65° C. for 30 min
  8. customafter which it was partitioned between EtOAc and 1 M NaOH
  9. customThe organic layer was separated
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. customto provide a residue that

Sources & evidence

ORD record
ord-54e7e43e1a5d44eaaff5be25e4a092aa
Source dataset
uspto-grants-2014_09
Patent number
US08846909B2

Reaction notes

Loading…