Triethylamine → HCID 178441442, compound

HRID 2425509Notes

Reaction equation

HRID 2425509 reaction equation
C(OCCCC)(=O)C.C(N(CC)CC)C.[CH2:16]([C:20]1[N:24]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[C:38]#[N:39])=[CH:28][CH:27]=2)[C:23](=[O:40])[C:22]2([CH2:44][CH2:43][CH2:42][CH2:41]2)[N:21]=1)[CH2:17][CH2:18][CH3:19].[N-:45]=[N+:46]=[N-:47].[Na+]>C(O)(=O)C>[CH2:16]([C:20]1[N:24]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[C:38]3[NH:47][N:46]=[N:45][N:39]=3)=[CH:28][CH:27]=2)[C:23](=[O:40])[C:22]2([CH2:41][CH2:42][CH2:43][CH2:44]2)[N:21]=1)[CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31272Butyl AcetateHCID 33557Sodium AzideHCID 98431164'-((2-Butyl-4-oxo-1,3-diazaspiro(4.4)non-1-ene-3-yl)methyl)(1,1'-biphenyl)-2-carbonitrile

Product 1

HCID 178441442HCID 178441442, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
117.5 °C

Procedure

A RB flask was charged with n-butyl Acetate (50 ml), triethyl amine (22 ml) and acetic acid (9 ml) and stirred. 2-(n-butyl)-3-[[2′-(cyano)biphenyl-4-yl]methyl]-1,3-diazaspiro[4.4]non-1-en-4-one (10 g) and sodium Azide (3.4 g) was added to the flask and the reaction mixture was heated at 115-120° C. for 24 hrs, followed by cooling. The reaction was then quenched by addition of water (30 ml). The pH of the aqueous layer was adjusted between 10 to 11 with 30% Sodium hydroxide and then stirred for 10 min. Layers were separated and oily layer was treated with water and xylene. The pH of the aqueous layer was adjusted between 2 and 3 by the addition of hydrochloric acid and then stirred for 1 hour, filtered to obtain solid material which was washed with water (20 ml) and ethyl Acetate (5 ml) and dried at 90-100° C.

Workup

  1. temperatureby cooling
  2. customThe reaction was then quenched by addition of water (30 ml)
  3. stirringstirred for 10 min
  4. customLayers were separated
  5. additionoily layer was treated with water and xylene
  6. additionThe pH of the aqueous layer was adjusted between 2 and 3 by the addition of hydrochloric acid
  7. stirringstirred for 1 hour
  8. filtrationfiltered
  9. customto obtain solid material which
  10. washwas washed with water (20 ml) and ethyl Acetate (5 ml)
  11. customdried at 90-100° C.

Sources & evidence

ORD record
ord-d3b552f0fb694a7288882d3a39abd35d
Source dataset
uspto-grants-2011_06
Patent number
US07964737B2

Reaction notes

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