Ammonium formate → HCID 59353051, compound

HRID 1914726Notes

Reaction equation

HRID 1914726 reaction equation
C([O:8][CH2:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([S:19]([NH:22][C:23]2[C:32]([NH:33][C:34]3[CH:39]=[C:38]([O:40][CH3:41])[CH:37]=[CH:36][C:35]=3[CH2:42][CH2:43][CH2:44][OH:45])=[N:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]=2)(=[O:21])=[O:20])[CH:14]=1)=[O:11])C1C=CC=CC=1.C([O-])=O.[NH4+]>CCO.[Pd]>[OH:8][CH2:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([S:19]([NH:22][C:23]2[C:32]([NH:33][C:34]3[CH:39]=[C:38]([O:40][CH3:41])[CH:37]=[CH:36][C:35]=3[CH2:42][CH2:43][CH2:44][OH:45])=[N:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]=2)(=[O:21])=[O:20])[CH:14]=1)=[O:11]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 24996596HCID 24996596, compound

Product 1

HCID 59353051HCID 59353051, compoundYield 76.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

To a mixture of 2-(benzyloxy)-N-(3-{[(3-{[2-(3-hydroxypropyl)-5-methoxyphenyl]amino}quinoxalin-2-yl)amino]sulfonyl}phenyl)acetamide (69 mg; 0.1 mmol; 1 eq) in EtOH (12 mL) are added ammonium formate (69.3 mg; 1.1 mmol; 10 eq) and palladium on charcoal (10 mg, 10%). The reaction mixture is stirred at reflux for 2 h. The catalyst is filtered through celite, washed with EtOH and the filtrate is concentrated under reduced pressure to give a yellow residue. It is suspended in EtOH (2 mL), sonicated, filtered off and washed with EtOH (400 μL). The solid is dried in vacuo to give 41 mg (70%) of the title compound as a yellow solid 1H NMR (DMSO-d6) δ 12.53 (br s, 1H), 10.00 (s, 1H), 8.73 (s, 1H), 8.45 (s, 1H), 8.19 (br s, 1H), 7.99-7.91 (m, 2H), 7.75 (d, J=7.4 Hz, 1H), 7.57-7.48 (m, 2H), 7.42-7.32 (m, 2H), 7.09 (d, J=8.3 Hz, 1H), 6.68-6.61 (m, 1H), 5.75-5.62 (m, 1H), 4.45-4.30 (m, 1H), 4.00 (s, 2H), 3.70 (s, 3H), 3.28-3.15 (m, 4H), 1.58-1.45 (m, 2H). HPLC (max plot) 99%; Rt 3.71 min. UPLC/MS (ES−) 538.2, (ES−) 536.3.

Workup

  1. temperatureat reflux for 2 h
  2. filtrationThe catalyst is filtered through celite
  3. washwashed with EtOH
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. customto give a yellow residue
  6. customsonicated
  7. filtrationfiltered off
  8. washwashed with EtOH (400 μL)
  9. customThe solid is dried in vacuo

Sources & evidence

ORD record
ord-9697d5439b674fc78debc40cd4a8c91c
Source dataset
uspto-grants-2013_12
Patent number
US08614215B2

Reaction notes

Loading…