Hydrochloric Acid → HCID 67997632, compound

HRID 718729Notes

Reaction equation

HRID 718729 reaction equation
[C:1]([NH:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[C:7](=[O:38])[N:8]([C:15]1([CH2:23][CH2:24][CH2:25][CH2:26][NH:27]C(=O)OCC3C=CC=CC=3)[CH2:20][CH2:19][C:18](=[O:21])[NH:17][C:16]1=[O:22])[C:9]2=[O:14])(=[O:3])[CH3:2].[H][H].[ClH:41]>C(O)C.[Pd]>[ClH:41].[NH2:27][CH2:26][CH2:25][CH2:24][CH2:23][C:15]1([N:8]2[C:7](=[O:38])[C:6]3[C:10](=[CH:11][CH:12]=[CH:13][C:5]=3[NH:4][C:1](=[O:3])[CH3:2])[C:9]2=[O:14])[CH2:20][CH2:19][C:18](=[O:21])[NH:17][C:16]1=[O:22]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 86660589HCID 86660589, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 67997632HCID 67997632, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 15 (0.02 g, 0.038 mmol) in 2% HCl in ethanol (2.0 mL) was added palladium on activated charcoal (0.004 g) under an atmosphere of argon. The mixture was subsequently saturated with hydrogen using a hydrogen balloon. After 2 h, the mixture was flushed with argon, filtered and concentrated. Preparative HPLC afforded 16 (0.002 g, 12%). 1H NMR (400 MHz, D2O) δ 8.37 (s, 2H), 8.16 (d, J=8.5 Hz, 1H), 7.76 (dd, J=12.9, 5.5 Hz, 1H), 7.60 (d, J=7.4 Hz, 1H), 2.95 (t, J=7.6 Hz, 2H), 2.73 (m, 3H), 2.61-2.47 (m, 1H), 2.41-2.10 (m, 4H), 1.80-1.59 (m, 2H), 1.43 (d, J=39.6 Hz, 3H). MS (ESI) m/z calcd for C19H23N4O5 [M-Cl]+387.4, found 387.7.

Workup

  1. customthe mixture was flushed with argon
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-682aa521d0d4489c8a6f43f44fee0bfc
Source dataset
uspto-grants-2015_11
Patent number
US09193989B2

Reaction notes

Loading…