Hydrochloric Acid → HCID 67997624, compound

HRID 718724Notes

Reaction equation

HRID 718724 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:35])[N:5]([C:12]1([CH2:20][CH2:21][CH2:22][CH2:23][NH:24]C(=O)OCC3C=CC=CC=3)[CH2:17][CH2:16][C:15](=[O:18])[NH:14][C:13]1=[O:19])[C:6]2=[O:11].[H][H].[ClH:38]>C(O)C.[Pd]>[ClH:38].[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:35])[N:5]([C:12]1([CH2:20][CH2:21][CH2:22][CH2:23][NH2:24])[CH2:17][CH2:16][C:15](=[O:18])[NH:14][C:13]1=[O:19])[C:6]2=[O:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 86660586HCID 86660586, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 67997624HCID 67997624, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 6 (0.111 g, 0.232 mmol) in 2% HCl in ethanol (60 mL) was added palladium on activated charcoal (0.025 g) under an atmosphere of argon. The mixture was subsequently saturated with hydrogen using a hydrogen balloon. After 4 h, the mixture was flushed with argon, filtered using ethanol and methanol. Preparative HPLC afforded 7 (0.055 g, 69%) as a bright yellow solid. 1H NMR (400 MHz, DMSO) δ 8.31 (s, 1H), 7.52-7.34 (m, 1H), 6.94 (m, 2H), 6.53 (br s, 2H), 2.74 (t, J=7.4 Hz, 2H), 2.65 (m, 1H), 2.63-2.56 (m, 1H), 2.54 (m, 1H), 2.44 (m, 1H), 2.31 (m, 1H), 2.21 (m, 1H), 2.02 (m, 1H), 1.52 (m, 1H), 1.48-1.38 (m, 1H), 1.26 (m, 2H). MS (ESI) m/z calcd for C17H21N4O4 [M+H]+ 345.4, found 345.7.

Workup

  1. customthe mixture was flushed with argon
  2. filtrationfiltered

Sources & evidence

ORD record
ord-abf40bfe96ac43329356212499a9612e
Source dataset
uspto-grants-2015_11
Patent number
US09193989B2

Reaction notes

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