Ammonium Chloride → HCID 178452178, compound

HRID 2242194Notes

Reaction equation

HRID 2242194 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][NH:14][C:15](=[O:24])[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]#[N:23])[CH:17]=2)[CH2:10][C@H:9]1[C:25]([N:27]1[CH2:31][CH2:30][S:29][CH2:28]1)=[O:26])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:32]=[N+:33]=[N-:34].[Na+].[Cl-].[NH4+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][NH:14][C:15](=[O:24])[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]3[NH:34][N:33]=[N:32][N:23]=3)[CH:17]=2)[CH2:10][C@H:9]1[C:25]([N:27]1[CH2:31][CH2:30][S:29][CH2:28]1)=[O:26])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 69239419HCID 69239419, compound

Product 1

HCID 178452178HCID 178452178, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Example 30A (300 mg, 0.67 mmol) in anhydrous DMF (4 mL) was added sodium azide (522 mg, 8.04 mmol) followed by ammonium chloride (428.8 mg, 8.04 mmol). The mixture was flushed with nitrogen, then exposed to microwave irradiation (20 W, 175° C.) for 15 minutes. The mixture was concentrated under reduced pressure to afford a brown oil. The brown oil was purified by RP-HPLC to provide the titled compound. MS (ESI) m/e 488 (M+H)+, 486 (M−H)−; 1H NMR (300 MHz, CD3OD) δ ppm 1.39 (s, 6 H) 1.47 (s, 3 H) 1.68 (m, 1 H) 1.94 (m, 1 H) 2.59 (m, 2 H) 3.02 (m, 1 H) 3.14 (m, 1 H) 3.23 (m, 1 H) 3.48 (m, 2 H) 3.79 (m, 2 H) 4.56 (m, 2 H) 4.72 (m, 1 H) 7.55 (t, 1 H) 7.82 (d, 1 H) 8.18 (dd, 1 H) 8.44 (s, 1 H).

Workup

  1. customThe mixture was flushed with nitrogen
  2. customexposed to microwave irradiation (20 W, 175° C.) for 15 minutes
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customto afford a brown oil
  5. customThe brown oil was purified by RP-HPLC

Sources & evidence

ORD record
ord-86601e1e51e544faa827f3a35baa5f4e
Source dataset
uspto-grants-2010_03
Patent number
US07671076B2

Reaction notes

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