Ammonia → HCID 59130345, compound

HRID 1992304Notes

Reaction equation

HRID 1992304 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[C:11]([NH:13][C:14]1[CH:18]=[CH:17][S:16][C:15]=1[C:19]([OH:21])=O)=[O:12].Cl.C[N:24](C)CCCN=C=NCC.N>CN(C)C1C=CN=CC=1.C(Cl)Cl>[NH2:24][C:19]([C:15]1[S:16][CH:17]=[CH:18][C:14]=1[NH:13][C:11]([C:2]1[CH:3]=[N:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]=1)=[O:12])=[O:21]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 43358068HCID 43358068, compound

Product 1

HCID 59130345HCID 59130345, compoundYield 46.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-[(2-quinoxalinylcarbonyl)amino]-2-thiophenecarboxylic acid (0.70 g, 2.3 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (EDC, 2.24 g, 11.5 mmol), and 4-(dimethylamino)pyridine (DMAP, 1.43 g, 11.5 mmol) in CH2Cl2 (100 mL) was stirred at room temperature for 2 h. To the reaction mixture was added aqueous ammonia (40%, 5 mL), and the stirring continued for another 12 h. The solvent was evaporated to dryness and the resulting solid was washed with satd NH4Cl solution (3×), NaHCO3 solution and H2O. The organic phase was evaporated to dryness resulting in a white powder (0.32 g, 46%). HPLC/MS: (M+H)+ 299.4 m/z

Workup

  1. waitthe stirring continued for another 12 h
  2. customThe solvent was evaporated to dryness
  3. washthe resulting solid was washed with satd NH4Cl solution (3×), NaHCO3 solution and H2O
  4. customThe organic phase was evaporated to dryness

Sources & evidence

ORD record
ord-c5744e0517574c64858f51c20aa70788
Source dataset
uspto-grants-2010_01
Patent number
US07648986B2

Reaction notes

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