Triethylamine → HCID 57732086, compound

HRID 401740Notes

Reaction equation

HRID 401740 reaction equation
[S:1]1[CH:5]=[N:4][N:3]=[C:2]1[NH:6][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:49][C:50]([F:60])([F:59])[C:51]1[CH:58]=[CH:57][C:54]([CH2:55][NH2:56])=[CH:53][CH:52]=1>C1COCC1>[S:1]1[CH:5]=[N:4][N:3]=[C:2]1[NH:6][S:7]([C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([NH:56][CH2:55][C:54]1[CH:53]=[CH:52][C:51]([C:50]([F:49])([F:59])[F:60])=[CH:58][CH:57]=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 28375123HCID 28375123, compound

Product 1

HCID 57732086HCID 57732086, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
35 °C

Procedure

To a solution of 3-[(1,3,4-thiadiazol-2-ylamino)sulfonyl]benzoic acid (100 mg, 0.350, mmol, 1 eq) in THF (1 ml) was added Et3N (0.19 ml, 1.4 mmol, 4 eq), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI HCl, 87 mg, 0.455 mmol, 1.3 eq), 1-hydroxybenzotriazole hydrate (HOBt, 61 mg, 0.455 mmol, 1.3 eq) and 4-(trifluoromethyl)benzylamine (0.075 ml, 0.525 mmol, 1.5 eq) at 0° C. The reaction mixture was stirred at 30-40° C. for 18 hours. The reaction mixture was extracted from 2M HCl into ethyl acetate, washed with sat sodium hydrogen carbonate, brine, dried over magnesium sulphate, filtered and evaporated in vacuo. The crude material was purified by preparative HPLC to yield the title compound.

Workup

  1. extractionThe reaction mixture was extracted from 2M HCl into ethyl acetate
  2. washwashed
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe crude material was purified by preparative HPLC

Sources & evidence

ORD record
ord-dfafd6963e77487eb6f4108053c9bf3e
Source dataset
uspto-grants-2014_06
Patent number
US08741934B2

Reaction notes

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