Propanal → HCID 10424901, compound

HRID 1611700Notes

Reaction equation

HRID 1611700 reaction equation
[CH3:1][CH:2]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([NH2:19])[CH:15]=[CH:14]2)[CH2:3][C:4]([CH3:7])([CH3:6])[CH3:5].C([BH3-])#N.[CH:23](=O)[CH2:24][CH3:25]>CO.C(Cl)CCl>[CH2:23]([NH:19][C:16]1[CH:15]=[CH:14][C:13]2[C:18](=[C:9]([O:8][CH:2]([CH3:1])[CH2:3][C:4]([CH3:7])([CH3:6])[CH3:5])[CH:10]=[CH:11][CH:12]=2)[N:17]=1)[CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 527PropanalHCID 498716Cyano-borohydrideHCID 10083869HCID 10083869, compound

Product 1

HCID 10424901HCID 10424901, compound

Reagents, catalysts & solvents 1

HCID 22134543HCID 22134543, compoundSolvent

Procedure

To a 4 mL scintillation vial was added a stir bar and the title compound from Example 16 (15.0 mg, 0.058 mmol). To this was added 0.42 mL of a 1:1 MeOH/ClCH2CH2Cl mixture followed by MP-cyanoborohydride resin (84 mg, 3.7 equiv Argonaut Technologies, Inc.) and 40 μL (10 equiv) of propionaldehyde. The reaction vessel was placed in an oil bath that had been preheated to 80° C. and the contents were allowed to stir overnight. Upon cooling to room temperature, the suspension was filtered and the filtrate was evaporated in vacuo. The crude material was purified by reverse phase HPLC to afford the title compound. 1H NMR (500 MHz, CDCl3) δ ppm 8.06 (d, 1H), 7.30 (m, 1H), 7.17 (m, 2H), 6.90 (d, 1H), 4.54–4.81 (m, 1H), 3.38 (m, 2H), 2.38 (m, 1H), 1.80 (m, 1H), 1.50 (m, 2H), 1.39 (d, 3H), 1.03 (t, 3H), 0.96 (s, 9H); MS (DCI/NH3) m/z 301 [M+H]+.

Workup

  1. additionTo a 4 mL scintillation vial was added a stir bar
  2. customThe reaction vessel was placed in an oil bath
  3. customhad been preheated to 80° C.
  4. filtrationthe suspension was filtered
  5. customthe filtrate was evaporated in vacuo
  6. customThe crude material was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-f8d54dcd541b4b0ab9275e5aaf4b6249
Source dataset
uspto-grants-2006_01
Patent number
US06989392B2

Reaction notes

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