Diisopropylethylamine → 3-Bromo-N-((6-methylpyridin-3-yl)methyl)-5-(methylsulfonyl)benzamide

HRID 1845220Notes

Reaction equation

HRID 1845220 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:10]=1)[C:5]([OH:7])=O.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[CH3:38][C:39]1[N:44]=[CH:43][C:42]([CH2:45][NH2:46])=[CH:41][CH:40]=1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:10]=1)[C:5]([NH:46][CH2:45][C:42]1[CH:43]=[N:44][C:39]([CH3:38])=[CH:40][CH:41]=1)=[O:7]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 12214337(6-Methylpyridin-3-yl)methanamineHCID 543046163-Bromo-5-methanesulfonylbenzoic acid

Product 1

HCID 581882653-Bromo-N-((6-methylpyridin-3-yl)methyl)-5-(methylsulfonyl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 3-bromo-5-(methylsulfonyl)benzoic acid (630 mg, 2.2 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (860 mg, 4.5 mmol), 1-hydroxybenzotriazole hydrate (140 mg, 0.90 mmol), and CH2Cl2 (25 mL) were added (6-methylpyridin-3-yl)methanamine (550 mg, 4.5 mmol) and N,N-diisopropylethylamine (0.79 mL, 4.5 mmol). The mixture was stirred at room temperature overnight, and then diluted with CH2Cl2 (50 mL). The organic phase was washed with water and aq. Na2CO3 solution, dried (Na2SO4), and concentrated in vacuo. The residue was purified by silica gel column (50-100% EtOAc/hexane) to afford a white solid. LC-MS: 385.2 [M+1]+; 1H NMR (400 MHz, CDCl3): 8.51 (d, 1H, J=1.6 Hz), 8.28 (t, 1H, J=1.6 Hz), 8.23 (t, 1H, J=1.6 Hz), 8.19 (t, 1H, J=1.6 Hz), 7.66 (dd, 1H, J=8.0, 2.0 Hz), 7.19 (d, 1H, J=8.0 Hz), 6.93 (bs, 1H), 4.63 (d, 2H, J=5.6 Hz), 3.09 (s, 3H), 2.57 (s, 3H).

Workup

  1. washThe organic phase was washed with water and aq. Na2CO3 solution
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel column (50-100% EtOAc/hexane)
  5. customto afford a white solid

Sources & evidence

ORD record
ord-39163098d6fc4c11886721710a410ad9
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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