4-Nitrobenzoyl chloride → HCID 58865679, compound

HRID 1354834Notes

Reaction equation

HRID 1354834 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][C@H:13]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][N:11]([C:23]2[C:32]([N:33]3[CH2:38][C@@H:37]([NH:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:36][C@@H:35]([NH:47][C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[CH2:34]3)=[N:31][C:30]3[C:25](=[CH:26][CH:27]=[C:28]([NH2:55])[CH:29]=3)[N:24]=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N+:56]([C:59]1[CH:67]=[CH:66][C:62]([C:63](Cl)=[O:64])=[CH:61][CH:60]=1)([O-:58])=[O:57].C(N(C(C)C)C(C)C)C.CCCCCC.CCOC(C)=O>CN(C=O)C.CCOC(C)=O>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][C@H:13]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][N:11]([C:23]2[C:32]([N:33]3[CH2:34][C@@H:35]([NH:47][C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[CH2:36][C@@H:37]([NH:39][C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:38]3)=[N:31][C:30]3[C:25](=[CH:26][CH:27]=[C:28]([NH:55][C:63](=[O:64])[C:62]4[CH:61]=[CH:60][C:59]([N+:56]([O-:58])=[O:57])=[CH:67][CH:66]=4)[CH:29]=3)[N:24]=2)[CH2:10]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 85024-Nitrobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 21226206Ethyl acetate hexaneHCID 58865622HCID 58865622, compound2×

Product 1

HCID 58865679HCID 58865679, compoundYield 78.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2,3-bis-((3R,5S)-3,5-bis-(tert-Butoxycarbonylamino)-piperidin-1-yl)-quinoxalin-6-ylamine (246) (0.067 g, 0.087 mmol) and p-nitro-benzoylchloride (0.0167 g, 0.09 mmol) were combined and dissolved in DMF (0.45 mL). iPr2EtN (0.016 mL, 0.09 mmol) was added and the mixture was shaken at room temperature for 16 h. TLC (Rf: 0.8 compared to Rf: 0.05 for compound 246 in 1:1 hexane/EtOAc) and LC-MS indicated complete coupling at this point. The mixture was diluted with EtOAc (30 mL), washed with saturated aqueous NaHCO3 (2×10 mL) and brine (2×10 mL) via extraction, dried over MgSO4 and concentrated to give the desired product (251) as an orange solid (0.063 g, 0.068 mmol, 78.6% yield). LC-MS (ESI): (exact mass: 920.48) m/e=921.8 [M+1]+.

Workup

  1. washwashed with saturated aqueous NaHCO3 (2×10 mL) and brine (2×10 mL) via extraction
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d9946f841be24b5d97c76ae1d573484c
Source dataset
uspto-grants-2007_05
Patent number
US07223759B2

Reaction notes

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