Hydrochloric Acid → HCID 57901855, compound

HRID 1851581Notes

Reaction equation

HRID 1851581 reaction equation
[CH3:1][N:2]([C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:22]=1[NH:21][C:20]([C:23]1[S:24][CH:25]=[CH:26][N:27]=1)=[CH:19]2)[S:3]([C:6]1[CH:10]=[CH:9][S:8][C:7]=1[C:11](O)=[O:12])(=[O:5])=[O:4].N1(O)C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[NH:50]1[CH2:55][CH2:54][O:53][CH2:52][CH2:51]1.Cl>CN(C)C=O>[CH3:1][N:2]([C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:22]=1[NH:21][C:20]([C:23]1[S:24][CH:25]=[CH:26][N:27]=1)=[CH:19]2)[S:3]([C:6]1[CH:10]=[CH:9][S:8][C:7]=1[C:11]([N:50]1[CH2:55][CH2:54][O:53][CH2:52][CH2:51]1)=[O:12])(=[O:5])=[O:4]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57901570HCID 57901570, compound

Product 1

HCID 57901855HCID 57901855, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-({methyl[2-(1,3-thiazol-2-yl)-1H-indol-7-yl]amino}sulfonyl)thiophene-2-carboxylic acid (100 mg), 1H-1,2,3-benzotriazol-1-ol (46 mg) and N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (58 mg) in N,N-dimethylformamide (2 mL) was added morpholine (100 μL), and the mixture was stirred at room temperature for 12 hr. To the reaction mixture was added 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was crystallized from diethyl ether-hexane to give the title compound (61 mg, yield 52%) as colorless crystals. melting point 190° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe obtained residue was crystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-bc6aff6acc4d43c3860b779267708107
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

Loading…