4-Methylmorpholine → 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide

HRID 715762Notes

Reaction equation

HRID 715762 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.[N:10]1[CH:11]=[CH:12][N:13]2[CH:18]=[CH:17][C:16]([CH2:19][NH2:20])=[CH:15][C:14]=12.O.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.C(OCC)(=O)C.O>[Br:1][C:2]1[S:6][C:5]([C:7]([NH:20][CH2:19][C:16]2[CH:17]=[CH:18][N:13]3[CH:12]=[CH:11][N:10]=[C:14]3[CH:15]=2)=[O:9])=[CH:4][CH:3]=1

Participants

9

Reactant 5

HCID 79724-MethylmorpholineHCID 3491155-Bromothiophene-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 55289825Imidazo(1,2-a)pyridin-7-ylmethanamine

Product 1

HCID 867019355-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-bromothiophene-2-carboxylic acid (1.279 g, 6.18 mmol), imidazo[1,2-a]pyridin-7-ylmethanamine (1 g, 6.79 mmol), 1-hydroxybenzotriazole hydrate (1.041 g, 6.79 mmol) and N-methylmorpholine (1.698 ml, 15.44 mmol) in dimethylformamide (20 ml) at room temperature was treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.131 g, 11.12 mmol). The mixture was stirred overnight and poured into a gently stirred round-bottom flask containing water (100 ml) and ethyl acetate (30 ml). The resulting bilayer suspension was stirred for several minutes, filtered and washed with water then minimal ethyl acetate to give the title compound after drying.

Workup

  1. additionpoured into a gently stirred round-bottom flask
  2. stirringThe resulting bilayer suspension was stirred for several minutes
  3. filtrationfiltered
  4. washwashed with water

Sources & evidence

ORD record
ord-6548a29ee8924a9b845cc1f4728a0b00
Source dataset
uspto-grants-2015_11
Patent number
US09187472B2

Reaction notes

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