Acetaldehyde → HCID 73505015, compound

HRID 590825Notes

Reaction equation

HRID 590825 reaction equation
[NH2:1][C:2]1[C:6]2[C:7]([CH2:23][O:24][CH3:25])=[N:8][C:9]([NH:11][C:12]([NH:14][C@@H:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH3:16])=[O:13])=[CH:10][C:5]=2[NH:4][N:3]=1.[O-]S([O-])(=O)=O.[Mg+2].[C:32](O)([C:34](F)(F)F)=O.C(=O)C.C([BH3-])#N.[Na+]>C(Cl)(Cl)Cl.CO>[CH2:32]([NH:1][C:2]1[C:6]2[C:7]([CH2:23][O:24][CH3:25])=[N:8][C:9]([NH:11][C:12]([NH:14][C@@H:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH3:16])=[O:13])=[CH:10][C:5]=2[NH:4][N:3]=1)[CH3:34]

Participants

8

Reactant 5

HCID 177AcetaldehydeHCID 6422Trifluoroacetic acidHCID 24083Sulfuric acid magnesium salt (1:1)HCID 5003444Sodium cyanoborohydrideHCID 73505014HCID 73505014, compound

Product 1

HCID 73505015HCID 73505015, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

A solution of (R)-1-(3-amino-4-(methoxymethyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea (34.8 mg, 0.102 mmol) in chloroform (0.6 ml) and MeOH (0.3 ml) was charged with MgSO4 (45 mg, 0.374 mmol), TFA (24 μl, 0.312 mmol) and acetaldehyde (0.02 ml, 0.354 mmol). The mixture was stirred at RT for 1 hr, then charged with sodium cyanoborohydride (22 mg, 0.350 mmol) before it was stirred at RT for 1.5 hr. The mixture was filtered to remove insoluble matter, rinsing with MeOH and DCM and concentrated in vacuo. The residue was purified by mass-triggered reverse-phase HPLC to provide (R)-1-(3-(ethylamino)-4-(methoxymethyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea. MS ESI calc'd for C19H25N6O2 [M+H]+ 369. found 369. 1H NMR (ppm, 500 MHz, DMSO-d6) δ 11.64 (s, 1H), 8.96 (s, 1H), 7.33 (m, 4H), 7.23 (m, 1H), 7.15 (s, 1H), 5.56 (t, J=6.5 Hz, 1H), 4.85 (t, J=7.3 Hz), 4.63 (m, 2H), 3.32 (s, 3H, overlaps with H2O peak), 3.22 (m, 2H), 1.39 (d, 6.8 Hz, 3H), 1.20 (t, J=4.9 Hz, 3H).

Workup

  1. stirringwas stirred at RT for 1.5 hr
  2. filtrationThe mixture was filtered
  3. customto remove insoluble matter
  4. washrinsing with MeOH and DCM
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by mass-triggered reverse-phase HPLC

Sources & evidence

ORD record
ord-91b0ad1d6cb340de9e03937238ad4a15
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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