Aniline → HCID 86685986, compound

HRID 2277689Notes

Reaction equation

HRID 2277689 reaction equation
[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[Cl:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[C:22](=[O:26])[N:21]([C:27]1[CH:28]=[C:29]([CH:33]=O)[CH:30]=[N:31][CH:32]=1)[CH2:20][CH2:19]2.[NH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>CO>[Cl:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[C:22](=[O:26])[N:21]([C:27]1[CH:32]=[N:31][CH:30]=[C:29]([CH2:33][NH:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH:28]=1)[CH2:20][CH2:19]2

Participants

5

Reactant 3

HCID 6115AnilineHCID 5049666Sodium triacetoxyborohydrideHCID 86685987HCID 86685987, compound

Product 1

HCID 86685986HCID 86685986, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaBH(OAc)3 (84 mg, 0.4 mmol) was added to a solution of 5-(6-chloro-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl)-pyridine-3-carbaldehyde (28.6 mg, 0.1 mmol, example 9) and aniline (9.3 mg 0.1 mmol) in MeOH (3 mL) and the resulting reaction mixture was stirred at RT overnight before it was poured into ice-water and extracted with EtOAc (2×10 mL). The organic layers were dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product which was purified by prep-HPLC to give title compound (7.2 mg, 20%) as a white solid. MS: 364.2 (M+H+).

Workup

  1. customthe resulting reaction mixture
  2. extractionextracted with EtOAc (2×10 mL)
  3. customThe organic layers were dried over anhy
  4. filtrationNa2SO4, filtered
  5. concentrationconcentrated in vacuo
  6. customto give a crude product which
  7. customwas purified by prep-HPLC

Sources & evidence

ORD record
ord-2560994f13e246bebc32e185f1e93634
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

Loading…