Hydrochloric Acid → HCID 68183134, compound

HRID 1615543Notes

Reaction equation

HRID 1615543 reaction equation
[NH2:1][CH:2]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)[C:3]1[C:7]([C:8]#[N:9])=[C:6]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[S:5][C:4]=1[C:16]([OH:18])=O.Cl.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)C(C)C)(C)C>C(Cl)Cl.CO.C(Cl)Cl>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([CH:2]2[NH:1][C:16](=[O:18])[C:4]3[S:5][C:6]([N:10]4[CH2:15][CH2:14][O:13][CH2:12][CH2:11]4)=[C:7]([C:8]#[N:9])[C:3]2=3)=[CH:20][CH:21]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 66748187HCID 66748187, compound

Product 1

HCID 68183134HCID 68183134, compoundYield 74.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 21226129Dichloromethane methanolSolvent

Procedure

To a mixture of 3-[amino(4-chlorophenyl)methyl]-4-cyano-5-(morpholin-4-yl)thiophene-2-carboxylic acid.HCl (0.206 g, 0.497 mmol), 1-Hydroxybenzotriazole hydrate (92.1 mg, 0.601 mmol) and N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (188 mg, 0.981 mmol) in dry Methylene chloride (10.0 mL, 156 mmol) was added N,N-Diisopropylethylamine (0.252 mL, 1.45 mmol). The resulted clear solution was stirred at r.t. for 21 hours. The reaction solution was diluted with DCM (−30 mL), washed with water (3×), brine, dried over anhydrous Na2SO4, filtered and rotavaped to give a crude product. Chromatograph in a silica gel column using MeOH/DCM (0/100 to 3/97) afforded a racemic product (0.138 g, yield 74.8%).

Workup

  1. washwashed with water (3×), brine
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. customto give a crude product

Sources & evidence

ORD record
ord-d593eaa7c5d641f99bf9f3d404719506
Source dataset
uspto-grants-2014_07
Patent number
US08765746B2

Reaction notes

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