Ammonium Chloride → HCID 58795834, compound

HRID 1911781Notes

Reaction equation

HRID 1911781 reaction equation
[CH:1]1([CH2:4][N:5]([CH2:36][CH:37]2[CH2:39][CH2:38]2)[C:6]2[N:11]=[C:10]3[N:12]([CH3:16])[C:13]([CH3:15])=[N:14][C:9]3=[CH:8][C:7]=2[CH2:17][N:18]([CH2:21][C:22]2[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[C:24]([C:32]([F:35])([F:34])[F:33])[CH:23]=2)[C:19]#[N:20])[CH2:3][CH2:2]1.[N-:40]=[N+:41]=[N-:42].[Na+].[Cl-].[NH4+]>CN(C=O)C.C(OCC)(=O)C>[F:35][C:32]([F:33])([F:34])[C:24]1[CH:23]=[C:22]([CH:27]=[C:26]([C:28]([F:30])([F:29])[F:31])[CH:25]=1)[CH2:21][N:18]([CH2:17][C:7]1[CH:8]=[C:9]2[N:14]=[C:13]([CH3:15])[N:12]([CH3:16])[C:10]2=[N:11][C:6]=1[N:5]([CH2:4][CH:1]1[CH2:2][CH2:3]1)[CH2:36][CH:37]1[CH2:39][CH2:38]1)[C:19]1[N:40]=[N:41][NH:42][N:20]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 86718420HCID 86718420, compound

Product 1

HCID 58795834HCID 58795834, compoundYield 926.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of [5-(bis-cyclopropylmethyl-amino)-2,3-dimethyl-3H-imidazo[4,5-b]pyridin-6-ylmethyl]-(3,5-bis-trifluoromethyl-benzyl)-cyanamide (0.220 g, 0.04 mmol), sodium azide (0.130 g, 2 mmol.) and ammonium chloride (0.106 g, 2 mmol) were taken in DMF (15 mL) and heated at 90° C. for 2 h. The reaction mixture was taken in ethyl acetate (250 mL) and washed with water (250 mL×4) and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to yield 0.220 g of colorless gummy liquid.

Workup

  1. washwashed with water (250 mL×4)
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c7ffcf03edd24b7ab4dedf96f596d93d
Source dataset
uspto-grants-2013_12
Patent number
US08604055B2

Reaction notes

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