HCID 86660585, compound → HCID 86660586, compound

HRID 718723Notes

Reaction equation

HRID 718723 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6](=[O:37])[N:7]([C:14]1([CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27](=[O:36])[O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:19][CH2:18][C:17](=[O:20])[NH:16][C:15]1=[O:21])[C:8]2=[O:13])([O-])=O.[H][H]>C(O)C.[Ni]>[NH2:1][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6](=[O:37])[N:7]([C:14]1([CH2:22][CH2:23][CH2:24][CH2:25][NH:26][C:27](=[O:36])[O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:19][CH2:18][C:17](=[O:20])[NH:16][C:15]1=[O:21])[C:8]2=[O:13]

Participants

5

Reactant 2

HCID 86660585HCID 86660585, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 86660586HCID 86660586, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a suspension of 5 (0.24 g, 0.472 mmol) in ethanol (15 mL) was added Raney Nickel (W.R. Grace and Co. Raney® 4200, slurry, in H2O) under argon. The mixture was subsequently saturated with hydrogen using a hydrogen balloon. After 1.5 h, the mixture was flushed with argon, filtered using EtOH and concentrated. Purification by flash chromatography (95:5 DCM:MeOH) afforded 6 (0.112 mg, 49%) as a bright yellow solid. Rf=0.38 (95:5 DCM:MeOH). 1H NMR (400 MHz, DMSO) δ 10.97 (s, 1H), 9.09 (s, 1H), 9.04 (s, 1H), 7.71-7.52 (m, 2H), 7.49-7.18 (m, 5H), 7.10 (m, 1H), 5.07-4.85 (m, 2H), 2.96 (m, 2H), 2.55 (m, 2H), 2.44 (m, 1H), 2.22 (m, 2H), 2.02 (m, 1H), 1.40 (m, 2H), 1.22 (m, 2H). MS (ESI) m/z calcd for C25H27N4O6 [M+H]+ 479.5, found 479.9.

Workup

  1. customthe mixture was flushed with argon
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customPurification by flash chromatography (95:5 DCM:MeOH)

Sources & evidence

ORD record
ord-7c56b1c277d14d83a8a01dfa7155b128
Source dataset
uspto-grants-2015_11
Patent number
US09193989B2

Reaction notes

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