Sodium Azide → HCID 86662600, compound

HRID 1958050Notes

Reaction equation

HRID 1958050 reaction equation
Cl[CH2:2][C:3]([N:5]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:21]=1[CH3:27])[C:6]1[N:7]=[C:8]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[S:9][C:10]=1[C:11]#[N:12])=[O:4].[N-:28]=[N+:29]=[N-:30].[Na+]>CN(C)C=O.CCOC(C)=O>[N:28]([CH2:2][C:3]([N:5]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:21]=1[CH3:27])[C:6]1[N:7]=[C:8]([N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)[S:9][C:10]=1[C:11]#[N:12])=[O:4])=[N+:29]=[N-:30]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 66780405HCID 66780405, compound

Product 1

HCID 86662600HCID 86662600, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-chloro-N-[(3-chloro-2-methylphenyl)methyl]-N-[5-cyano-2-(4-morpholinyl)-1,3-thiazol-4-yl]acetamide (200 mg, 0.470 mmol) (prepared according to the procedures of example 59) in N,N-Dimethylformamide (DMF) (2 mL) was added sodium azide (92 mg, 1.410 mmol) at rt. The mixture was stirred at rt for 3 hr before diluted in 100 ml EtOAc and washed with 20 mL H2O twice. The organic layer was concentrated to give 200 mg crude product (99%), which was used in the next step without further purification. LC/MS (ES) m/z=432.2 (M+H).

Workup

  1. washwashed with 20 mL H2O twice
  2. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-1154dd8a87d64973a383cd679752c4fc
Source dataset
uspto-grants-2013_04
Patent number
US08410095B2

Reaction notes

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