Nitrogen → 6-[(1-Carbamoyl-1,2-dimethylpropyl)carbamoyl]thieno[2,3-b]pyridine-5-carboxylic acid

HRID 256121Notes

Reaction equation

HRID 256121 reaction equation
[NH2:1][C:2]([CH3:9])([CH:6]([CH3:8])[CH3:7])[C:3]([NH2:5])=[O:4].[S:10]1[C:14]2=[N:15][C:16]3[C:22](=[O:23])[O:21][C:19](=[O:20])[C:17]=3[CH:18]=[C:13]2[CH:12]=[CH:11]1.N#N>C1COCC1>[C:3]([C:2]([NH:1][C:22]([C:16]1[N:15]=[C:14]2[S:10][CH:11]=[CH:12][C:13]2=[CH:18][C:17]=1[C:19]([OH:21])=[O:20])=[O:23])([CH3:9])[CH:6]([CH3:8])[CH3:7])(=[O:4])[NH2:5]

Participants

5

Reactant 3

HCID 947NitrogenHCID 97937732-Amino-2,3-dimethylbutanamideHCID 13849605Thieno[2,3-b]pyridine-5,6-dicarboxylic acid anhydride

Product 1

HCID 140323636-[(1-Carbamoyl-1,2-dimethylpropyl)carbamoyl]thieno[2,3-b]pyridine-5-carboxylic acidYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Amino-2,3-dimethylbutyramide (9.84 g, 0.076 mol) is added to a stirred suspension of thieno[2,3-b]pyridine-5,6-dicarboxylic acid anhydride (14.8 g, 0.072 mol) in THF under an inert atmosphere of N2 at room temperature. The dark solution is stirred at room temperature overnight and the resulting solid filtered off, washed with THF and air dried to give 17.35 g (72%) of 6-[(1-carbamoyl-1,2-dimethylpropyl)carbamoyl]thieno[2,3-b]pyridine-5-carboxylic acid.

Workup

  1. filtrationthe resulting solid filtered off
  2. washwashed with THF and air
  3. customdried

Sources & evidence

ORD record
ord-7dc6a1ffa9a547779ae73a2617006d5c
Source dataset
uspto-grants-1987_10
Patent number
US04701208

Reaction notes

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