2-Amino-2,3-dimethylbutanamide → 5-[(1-Carbamoyl-1,2-dimethylpropyl)carbamoyl]3-chlorothieno[3,2-b]pyridine-6-carboxylic acid

HRID 2073964Notes

Reaction equation

HRID 2073964 reaction equation
[NH2:1][C:2]([CH3:9])([CH:6]([CH3:8])[CH3:7])[C:3]([NH2:5])=[O:4].[Cl:10][C:11]1[C:15]2=[N:16][C:17]3[C:23](=[O:24])[O:22][C:20](=[O:21])[C:18]=3[CH:19]=[C:14]2[S:13][CH:12]=1>C1COCC1>[C:3]([C:2]([NH:1][C:23]([C:17]1[N:16]=[C:15]2[C:11]([Cl:10])=[CH:12][S:13][C:14]2=[CH:19][C:18]=1[C:20]([OH:22])=[O:21])=[O:24])([CH3:9])[CH:6]([CH3:8])[CH3:7])(=[O:4])[NH2:5]

Participants

4

Reactant 2

HCID 97937732-Amino-2,3-dimethylbutanamideHCID 137524853-Chlorothieno[3,2-b]pyridine-5,6-dicarboxylic acid anhydride

Product 1

HCID 137525025-[(1-Carbamoyl-1,2-dimethylpropyl)carbamoyl]3-chlorothieno[3,2-b]pyridine-6-carboxylic acidYield 75.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Amino-2,3-dimethylbutyramide (0.71 g) all in one portion is added to a stirred solution of 3-chlorothieno[3,2-b]pyridine-5,6-dicarboxylic acid anhydride, (1.2 g) in THF (1.0 mL). After standing for five minutes, the ice bath is removed and the reaction stirred at room temperature for 28 hours. THF (5 mL) is added and the mixture heated at reflux for two hours and then set aside overnight. The cooled mixture is filtered and the collected solid washed with ether to give 1.4 g of the desired 5-[(1-carbamoyl-1,2-dimethylpropyl)carbamoyl]-3-chlorothieno[3,2-b]pyridine-6-carboxylic acid.

Workup

  1. customthe ice bath is removed
  2. additionTHF (5 mL) is added
  3. temperaturethe mixture heated
  4. temperatureat reflux for two hours
  5. waitset aside overnight
  6. filtrationThe cooled mixture is filtered
  7. washthe collected solid washed with ether

Sources & evidence

ORD record
ord-fa63c7dc9f4b48e58da6011752bc3af1
Source dataset
uspto-grants-1990_04
Patent number
US04920226

Reaction notes

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