Nitrogen → HCID 49838063, compound

HRID 1189438Notes

Reaction equation

HRID 1189438 reaction equation
N#N.[C:3]([C:6]1[S:10][C:9]([CH2:11][C:12]2[O:13][CH:14]=[C:15](C(N=[N+]=[N-])=O)[N:16]=2)=[CH:8][CH:7]=1)(=[O:5])[CH3:4].CC1(C2SC(C[C:34]3[O:35]C=C(C(N=[N+]=[N-])=O)[N:38]=3)=CC=2)OCCO1.[Cl:44][C:45]1[CH:52]=[CH:51][CH:50]=[CH:49][C:46]=1[CH2:47][OH:48]>C1(C)C(C)=CC=CC=1>[Cl:44][C:45]1[CH:52]=[CH:51][CH:50]=[CH:49][C:46]=1[CH2:47][O:48][C:34](=[O:35])[NH:38][C:15]1[N:16]=[C:12]([CH2:11][C:9]2[S:10][C:6]([C:3](=[O:5])[CH3:4])=[CH:7][CH:8]=2)[O:13][CH:14]=1

Participants

6

Reactant 4

HCID 947NitrogenHCID 288102-Chlorobenzyl alcoholHCID 86664913HCID 86664913, compoundHCID 866649142-[5-(2-Methyl-[1,3]dioxolan-2-yl)-thiophen-2-ylmethyl]-oxazole-4-carbonyl azide

Product 1

HCID 49838063HCID 49838063, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
140 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of a mixture of 2-(5-acetyl-thiophen-2-ylmethyl)-oxazole-4-carbonyl azide and 2-[5-(2-methyl-[1,3]dioxolan-2-yl)-thiophen-2-ylmethyl]-oxazole-4-carbonyl azide (138 mg) in xylene (0.5 mL) was heated to 140° C. for 5 min. 2-chlorobenzyl alcohol (144 mg, 1.00 mmol) was then added and the reaction mixture was further stirred at 140° C. for 5 min. The solvent was removed under reduced pressure. Purification of the residue by FC (20:1→1:1 hept-EA) followed by preparative HPLC gave the title compound as a white solid. LC-MS-conditions 07: tR=1.50 min, [M+H]+=391.10.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customPurification of the residue by FC (20:1→1:1 hept-EA)

Sources & evidence

ORD record
ord-9cd1f2d7682845cebc91aa4cb25fcd69
Source dataset
uspto-grants-2014_03
Patent number
US08674111B2

Reaction notes

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