HCID 86689282, compound → HCID 71621463, compound

HRID 537290Notes

Reaction equation

HRID 537290 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=O)[CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][CH3:22])[CH:15]=2)=[C:6]([NH:24][CH2:25][CH:26]([CH3:28])[CH3:27])[CH:5]=1)[CH3:2]>CC(O)=O>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]2[N:10]=[C:11]([CH2:12][O:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][CH3:22])[CH:15]=3)[N:24]([CH2:25][CH:26]([CH3:28])[CH3:27])[C:6]=2[CH:5]=1)[CH3:2]

Participants

3

Reactant 1

HCID 86689282HCID 86689282, compound

Product 1

HCID 71621463HCID 71621463, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A 250 mL flask fitted with a stir-bar, condenser, and an Ar inlet was charged with amine 50a (12.5 g, 32.3 mmol) and AcOH (120 mL). The resultant solution was heated in a 100° C. bath for 3 hr. The mixture was cooled and concentrated in vacuo to a pale, orange solid. The solid was partitioned with EtOAc (150 mL) and saturated NaHCO3 (100 mL). The organic phase was washed with brine (100 mL), filtered through phase separation paper, and concentrated in vacuo to an orange oil. The oil was crystallized with hexanes (25 mL), filtered, and rinsed with hexanes (2×15 mL). The material dried to give 9.9 g of Compound #1 as an off-white solid (83%). 1H NMR (300 MHz, CDCl3): δ 7.66 (d, 1H), 7.21 (t, 1H), 6.94 (dd, 1H), 6.82 (d, 1H), 6.71-6.62 (m, 2H), 6.56 (dd, 1H), 5.33 (s, 2H), 4.10 (qt, 2H), 4.05 (t, 2H), 4.03 (qt, 2H), 2.35 (nonet, 1H), 1.48 (t, 3H), 1.43 (t, 3H), 0.98 (d, 6H) ppm. HPLC analysis (0:10:90 H2O:A1:MeOH) showed a purity of 99% with a retention time of 4.6 min.

Workup

  1. customA 250 mL flask fitted with a stir-bar, condenser
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated in vacuo to a pale, orange solid
  4. customThe solid was partitioned with EtOAc (150 mL) and saturated NaHCO3 (100 mL)
  5. washThe organic phase was washed with brine (100 mL)
  6. filtrationfiltered through phase separation paper
  7. concentrationconcentrated in vacuo to an orange oil
  8. customThe oil was crystallized with hexanes (25 mL)
  9. filtrationfiltered
  10. washrinsed with hexanes (2×15 mL)
  11. customThe material dried

Sources & evidence

ORD record
ord-fdb0d540f5c94c98baaa7f288802fb59
Source dataset
uspto-grants-2014_10
Patent number
US08859780B2

Reaction notes

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