HCID 43708295, compound → HCID 60207714, compound

HRID 1776136Notes

Reaction equation

HRID 1776136 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N+:16]([O-])=O)=[O:8]>[Pd].CO>[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH2:16])=[O:8]

Participants

4

Reactant 1

HCID 43708295HCID 43708295, compound

Product 1

HCID 60207714HCID 60207714, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4 (6.40 g, 25.7 mmol), 10% Pd—C (0.5 g), and methanol (200 mL) was stirred under a hydrogen balloon at room temperature for 3 hours. The catalyst was filtered off and washed with additional methanol. Solvent was removed in vacuo to give 5.8 g of Template 1 as an off white solid LC-MS (M++1) 222. 1H NMR (DMSO-d6) δ 1.34 (m, 4H), 1.57 (m, 2H), 2.29 (t, J=5.4 Hz, 2H), 2.49 (br, s, 2H), 2.54 (t, J=5.4 Hz, 2H), 4.32 (br, s, 2H), 6.52 (dd, J=6 Hz, J=6 Hz, 1H), 6.70 (d, J=6 Hz, 1H), 6.87 (dd, J=6 Hz, J=6 Hz, 1H), 7.15 (d, J=6 Hz, 1H), 9.14 (br, s, 1H).

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with additional methanol
  3. customSolvent was removed in vacuo
  4. customto give 5.8 g of Template 1 as an off white solid LC-MS (M++1) 222

Sources & evidence

ORD record
ord-dd5a1121616046b58b0daef8047be6aa
Source dataset
uspto-grants-2016_02
Patent number
US09265734B2

Reaction notes

Loading…