Dimethylamine → HCID 178484132, compound

HRID 2373888Notes

Reaction equation

HRID 2373888 reaction equation
Cl[C:2]1[C:3]2[N:4]([C:8]([C@@H:17]3[CH2:20][C@H:19]([N:21]([CH3:23])[CH3:22])[CH2:18]3)=[N:9][C:10]=2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:5]=[CH:6][N:7]=1.[CH2:24]([O:31]C1C=C(C2N=C(C3CC(=O)C3)N3C=CN=C(Cl)C=23)C=CC=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C[NH:54]C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C>CC(O)=O.ClCCCl>[CH2:24]([O:31][C:13]1[CH:12]=[C:11]([C:10]2[N:9]=[C:8]([C@H:17]3[CH2:20][C@@H:19]([N:21]([CH3:23])[CH3:22])[CH2:18]3)[N:4]3[CH:5]=[CH:6][N:7]=[C:2]([NH2:54])[C:3]=23)[CH:16]=[CH:15][CH:14]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 674DimethylamineHCID 2724942TriacetoxyborohydrideHCID 598528193-{1-[3-(Benzyloxy)phenyl]-8-chloroimidazo[1,5-a]pyrazin-3-yl}cyclobutanoneHCID 178484131HCID 178484131, compound

Product 1

HCID 178484132HCID 178484132, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolvent

Procedure

cis-[3-(8-Chloro-1-phenyl-imidazo[1,5-a]pyrazin-3-yl)-cyclobutyl]-dimethyl-amine: An DCE solution of 3-{1-[3-(benzyloxy)phenyl]-8-chloroimidazo[1,5-a]pyrazin-3-yl}cyclobutanone was charged with dimethylamine (0.37 mmol, 0.19 mL) and then catalytic amount of AcOH (7 μL). The mixture was stirred at rt for 30 min before resin-bound triacetoxyborohydride (0.5 mmol, 240 mg) was added. Reaction mixture was stirred at rt for 16 h before the solution was filtered through a Buchner funnel to remove the resin. The filtrate was concentrated and the obtained oil was dissolved in DCM (15 mL), washed with saturated NaHCO3 solution (2×15 mL) and brine (2×15 mL). The solvent was dried over sodium sulfate and concentrated under reduced pressure. The title compound was obtained as a yellow greasy oil; MS (ES+): m/z 433 (100) [MH+].

Workup

  1. additionwas added
  2. customReaction mixture
  3. filtrationwas filtered through a Buchner funnel
  4. customto remove the resin
  5. concentrationThe filtrate was concentrated
  6. dissolutionthe obtained oil was dissolved in DCM (15 mL)
  7. washwashed with saturated NaHCO3 solution (2×15 mL) and brine (2×15 mL)
  8. dry with materialThe solvent was dried over sodium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b730c995c3a24c7198d8b3ce8edf8fb7
Source dataset
uspto-grants-2008_12
Patent number
US07459554B2

Reaction notes

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