Dichloromethane → 5-(2-(3-(2-aminoethyl)ureido)-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-tert-butylpyridine-3-sulfonamide

HRID 384746Notes

Reaction equation

HRID 384746 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:10]=[C:11]([C:15]2[CH:16]=[CH:17][C:18]3[N:19]([N:21]=[C:22]([NH:24][C:25](=[O:37])[NH:26][CH2:27][CH2:28][NH:29]C(=O)OC(C)(C)C)[N:23]=3)[CH:20]=2)[CH:12]=[N:13][CH:14]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)Cl>Cl>[NH2:29][CH2:28][CH2:27][NH:26][C:25](=[O:37])[NH:24][C:22]1[N:23]=[C:18]2[CH:17]=[CH:16][C:15]([C:11]3[CH:10]=[C:9]([S:6]([NH:5][C:1]([CH3:2])([CH3:3])[CH3:4])(=[O:8])=[O:7])[CH:14]=[N:13][CH:12]=3)=[CH:20][N:19]2[N:21]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 66815312tert-butyl 2-(3-(6-(5-(N-tert-butylsulfamoyl)pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)ureido)ethylcarbamate

Product 1

HCID 498206095-(2-(3-(2-aminoethyl)ureido)-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-tert-butylpyridine-3-sulfonamideYield 73.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

tert-butyl 2-(3-(6-(5-(N-tert-butylsulfamoyl)pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)ureido)ethylcarbamate (35 mg) was suspended in HCl (4M in dioxane, 2 mL) and DCM (2 mL) and the reaction mixture stirred overnight at room temperature. After this time the reaction mixture was pippetted slowly onto diethyl ether at −78° C. and maintained at this temperature for 20 minutes. The resultant white solid was filtered, washed with further diethyl ether and dried under vacuum to afford the title compound (21 mg).

Workup

  1. customwas pippetted slowly onto diethyl ether at −78° C.
  2. temperaturemaintained at this temperature for 20 minutes
  3. filtrationThe resultant white solid was filtered
  4. washwashed with further diethyl ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-521be1c1430b4642a7b3233fc8549e65
Source dataset
uspto-grants-2013_02
Patent number
US08367830B2

Reaction notes

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