Sodium Azide → HCID 178478884, compound

HRID 1598894Notes

Reaction equation

HRID 1598894 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][C:28]([OH:37])([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:27][CH2:26]2)[C:10]([C:12]2[NH:16][N:15]=[N:14][C:13]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[N-]=[N+]=[N-].[Na+].[Cl:42]C1C=C(C(CCN2CCC(O)(C3C=CC=CC=3)CC2)C(=O)C#CC2C=CC=CC=2)C=CC=1Cl>CN(C)C=O>[ClH:1].[ClH:42].[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][C:28]([OH:37])([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH2:27][CH2:26]2)[CH:10]([C:12]2[N:16]=[N:15][NH:14][C:13]=2[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[OH:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 18930289HCID 18930289, compoundHCID 178520012HCID 178520012, compound

Product 1

HCID 178478884HCID 178478884, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
35 °C

Procedure

5-[2-(3,4-Dichlorophenyl)-4-(4-hydroxy-4-phenyl-piperidino)butyroyl]-4-phenyl-(1H)-1,2,3-triazole. A suspension of sodium azide (38 mg) in N,N-dimethylformamide (1 mL) was treated dropwise with a solution of 4-(3,4-dichlorophenyl)-6-(4-hydroxy-4-phenyl-piperidino)-1-phenyl-1-hexyn-3-one (287 mg) in N,N-dimethylformamide (4 mL). The reaction mixture was warmed to 35° C. and was stirred for 3 hours. The reaction was quenched by addition of water and extracted with ethyl acetate. The organic extracts were combined, washed (water, brine) and evaporated to leave an orange syrup. The syrup was triturated with dichloromethane to afford the triazole as a pale tan powder (260 mg, 83%). NMR (d6-DMSO): 7.89 (m, 2), 7.63 (d, J=1.8 Hz, 1), 7.57 (d, J=8.3 Hz, 1), 7.45-7.17 (m,9), 5.24 (t, J=7.3 Hz, 1H, H-C(2')), 4.91 (broad s, 1H, O), 2.86-2.50 (m,7), 1.95-1.49 (m,5H).

Workup

  1. customThe reaction was quenched by addition of water
  2. extractionextracted with ethyl acetate
  3. washwashed (water, brine)
  4. customevaporated
  5. customto leave an orange syrup
  6. customThe syrup was triturated with dichloromethane

Sources & evidence

ORD record
ord-ae1533f41542424dbee256a5b9563a51
Source dataset
uspto-grants-1998_04
Patent number
US05739149

Reaction notes

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