1,1,1-Trimethoxybutane → HCID 178439946, compound

HRID 1890339Notes

Reaction equation

HRID 1890339 reaction equation
C([O:8][C:9]1[N:14]=[C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:12]([NH2:22])=[CH:11][CH:10]=1)C1C=CC=CC=1.[C:23](OC)(OC)(OC)[CH2:24][CH2:25][CH3:26]>C(O)(C(F)(F)F)=O>[C:16]1([N:15]2[C:13]3=[N:14][C:9]([OH:8])=[CH:10][CH:11]=[C:12]3[N:22]=[C:23]2[CH2:24][CH2:25][CH3:26])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 1235121,1,1-TrimethoxybutaneHCID 67312740HCID 67312740, compound

Product 1

HCID 178439946HCID 178439946, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 6-(benzyloxy)-N2-phenylpyridine-2,3-diamine (90 mg, 0.31 mmol), trimethyl orthobutyrate (5 mL), and TFA (20 μL) was stirred at room temperature for 2 h. The mixture was concentrated in vacuo and the residue dissolved in MeOH (5 mL). Palladium on carbon (20% wt./wt., 15 mg,) was added and the mixture was stirred vigorously under H2 (1 atm) for 1 h. The mixture was filtered through Celite® and concentrated to give the title compound as a white solid (26 mg). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.85 (t, J=7.6 Hz, 3H), 1.65 (s, J=7.3 Hz, 2H), 2.62 (t, J=7.6 Hz, 2H), 6.51 (d, J=8.6 Hz, 1H), 7.45-7.56 (m, 3H), 7.60 (t, J=7.6 Hz, 2H), 7.87 (d, J=8.3 Hz, 1H), 10.75 (br s, 1H).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionthe residue dissolved in MeOH (5 mL)
  3. additionPalladium on carbon (20% wt./wt., 15 mg,) was added
  4. stirringthe mixture was stirred vigorously under H2 (1 atm) for 1 h
  5. filtrationThe mixture was filtered through Celite®
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f9a3453814f74544a5d0d054efbe28cc
Source dataset
uspto-grants-2013_08
Patent number
US08507473B2

Reaction notes

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