Ethylamine → HCID 68835224, compound

HRID 2112978Notes

Reaction equation

HRID 2112978 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:19]3[N:20]=[C:21]([NH2:23])[N:22]=[C:18]3[CH:17]=[C:16]([C:24]3[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=3)[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].S([N:40]=[C:41]=[O:42])(C1C=CC(C)=CC=1)(=O)=O.[CH2:43](N)[CH3:44]>CN(C=O)C.C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[N:19]3[N:20]=[C:21]([NH:23][C:41]([NH:40][CH2:43][CH3:44])=[O:42])[N:22]=[C:18]3[CH:17]=[C:16]([C:24]3[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=3)[CH:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 6341EthylamineHCID 77703p-Toluenesulfonyl isocyanateHCID 68836927HCID 68836927, compound

Product 1

HCID 68835224HCID 68835224, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

The material produced in Step 1 (0.78 g, 2.0 mmol) was split into three batches. Each batch was suspended in DMF (3 mL) and then TsNCO (0.3 ml, 2 mmol) was added. The reaction mixture was stirred at rt overnight. Ethylamine (3 ml of a 2 M solution in THF, 6 mmol) was added and the resulting mixture was irradiated with microwaves at 130° C. for 40 minutes. The three batches were combined, filtered, washed with THF, and dried to afford 4-[2-(3-ethyl-ureido)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-piperazine-1-carboxylic acid tert-butyl ester as a solid. MS (APCI+) 467 (M+1).

Workup

  1. customthe resulting mixture was irradiated with microwaves at 130° C. for 40 minutes
  2. filtrationfiltered
  3. washwashed with THF
  4. customdried

Sources & evidence

ORD record
ord-77dce7dc2eac443093005091dc1823f6
Source dataset
uspto-grants-2009_04
Patent number
US07524860B2

Reaction notes

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