2,4,6-Tris((dimethylamino)methyl)phenol → N-[(5-methyl-1,3,4-thiadiazol-2-yl)methyl]-4-(2,4,6-trifluorobenzoyl)-1-H-pyrrole-2-carboxamide

HRID 1894716Notes

Reaction equation

HRID 1894716 reaction equation
CN(CC1C=C(CN(C)C)C(O)=C(CN(C)C)C=1)C.[F:20][C:21]1[CH:36]=[C:35]([F:37])[CH:34]=[C:33]([F:38])[C:22]=1[C:23]([C:25]1[CH:26]=[C:27]([C:30]([OH:32])=O)[NH:28][CH:29]=1)=[O:24].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.Cl.[CH3:63][C:64]1[S:68][C:67]([CH2:69][NH2:70])=[N:66][N:65]=1.C(N(C(C)C)CC)(C)C>>[CH3:63][C:64]1[S:68][C:67]([CH2:69][NH:70][C:30]([C:27]2[NH:28][CH:29]=[C:25]([C:23](=[O:24])[C:22]3[C:33]([F:38])=[CH:34][C:35]([F:37])=[CH:36][C:21]=3[F:20])[CH:26]=2)=[O:32])=[N:66][N:65]=1

Participants

7

Reactant 6

HCID 70262,4,6-Tris((dimethylamino)methyl)phenolHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 11615231(5-Methyl-1,3,4-thiadiazol-2-yl)methanamine hydrochlorideHCID 534025784-(2,4,6-Trifluorobenzoyl)-1H-pyrrole-2-carboxylic acid2×

Product 1

HCID 49784129N-[(5-methyl-1,3,4-thiadiazol-2-yl)methyl]-4-(2,4,6-trifluorobenzoyl)-1-H-pyrrole-2-carboxamideYield 69.3%

Procedure

To a DMF 3 mL solution of 4-(2,4,6-trifluorobenzoyl)-1-H-pyrrole-2-carboxylic acid (Intermediate 1) (30 mg, 0.11 mmol), 1-hydroxybenzotriazole hydrate (HOBT) (22 mg, 0.15 mmol) was added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide-hydrochloride (EDC-hydrochloride)(28 mg, 0.15 mmol). The reaction was stirred for 45 min before 1-(5-methyl-1,3,4-thiadiazol-2-yl)methanamine hydrochloride (19 mg, 0.17 mmol) and diisopropylethylamine (0.1 mL, 0.55 mmol) were added. The reaction mixture was stirred at rt overnight, concentrated and chromatographed on silica gel eluting with AcOEt to give the title compound 29 mg.

Workup

  1. additionwere added
  2. concentrationconcentrated
  3. customchromatographed on silica gel eluting with AcOEt

Sources & evidence

ORD record
ord-2253231ca8d441b7b415a3fdee4b5f1b
Source dataset
uspto-grants-2013_08
Patent number
US08513289B2

Reaction notes

Loading…