Triethylamine → HCID 57732180, compound

HRID 401739Notes

Reaction equation

HRID 401739 reaction equation
COC1C=C(OC)C=CC=1C[N:6]([C:19]1[S:20][CH:21]=[CH:22][N:23]=1)[S:7]([C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([OH:15])=O)(=[O:9])=[O:8].CCN(CC)CC.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[F:60][C:61]([F:71])([F:70])[C:62]1[CH:69]=[CH:68][C:65]([CH2:66][NH2:67])=[CH:64][CH:63]=1>C1COCC1>[S:20]1[CH:21]=[CH:22][N:23]=[C:19]1[NH:6][S:7]([C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([NH:67][CH2:66][C:65]1[CH:64]=[CH:63][C:62]([C:61]([F:60])([F:70])[F:71])=[CH:69][CH:68]=1)=[O:15])(=[O:8])=[O:9]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 768044-(Trifluoromethyl)benzylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 57732188HCID 57732188, compound

Product 1

HCID 57732180HCID 57732180, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-{[(2,4-Dimethoxybenzyl)(1,3-thiazol-2-yl)amino]sulfonyl}benzoic acid (Preparation 23, 90 mg, 0.207 mmol, 1 eq) THF (2 ml) was added Et3N (0.04 ml, 0.311 mmol, 1.5 eq), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI.HCl, 52 mg, 0.27 mmol, 1.3 eq) and 1-hydroxybenzotriazole hydrate (HOBt, 28 mg, 0.207 mmol, 1 eq) at 0° C. and the reaction mixture stirred for 10 minutes before the addition of 4-(trifluoromethyl)benzylamine (0.032 ml, 0.228 mmol, 1.1 eq). The reaction mixture was stirred at room temperature for 18 hours. The mixture was extracted from water into DCM, dried over magnesium sulphate, filtered and evaporated in vacuo. The residue was dissolved in 4M HCl in dioxane (2 ml) and the reaction mixture stirred at room temperature for 18 hours. The resulting precipitate was collected by filtration and washed with dioxane. The material was purified further by preparative HPLC to yield the title compound.

Workup

  1. extractionThe mixture was extracted from water into DCM
  2. dry with materialdried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. dissolutionThe residue was dissolved in 4M HCl in dioxane (2 ml)
  6. stirringthe reaction mixture stirred at room temperature for 18 hours
  7. filtrationThe resulting precipitate was collected by filtration
  8. washwashed with dioxane
  9. customThe material was purified further by preparative HPLC

Sources & evidence

ORD record
ord-dee994d57ecf4fdc9363714e7f0fb762
Source dataset
uspto-grants-2014_06
Patent number
US08741934B2

Reaction notes

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