Triethylamine → HCID 67345279, compound

HRID 1257678Notes

Reaction equation

HRID 1257678 reaction equation
[C:1]1([S:7]([N:10]2[CH:21]=[CH:20][C:19]3[C:11]2=[N:12][CH:13]=[C:14]2[C:18]=3[N:17]([C:22]3([CH3:28])[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[N:16]=[N:15]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[N:36]1[CH:41]=[CH:40][CH:39]=[C:38]([S:42](Cl)(=[O:44])=[O:43])[CH:37]=1>C(Cl)Cl>[C:1]1([S:7]([N:10]2[CH:21]=[CH:20][C:19]3[C:11]2=[N:12][CH:13]=[C:14]2[C:18]=3[N:17]([C:22]3([CH3:28])[CH2:27][CH2:26][N:25]([S:42]([C:38]4[CH:37]=[N:36][CH:41]=[CH:40][CH:39]=4)(=[O:44])=[O:43])[CH2:24][CH2:23]3)[N:16]=[N:15]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3164136Pyridine-3-sulfonyl chlorideHCID 67343253HCID 67343253, compound

Product 1

HCID 67345279HCID 67345279, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 6-benzenesulfonyl-1-(4-methyl-piperidine-4-yl)1,6-dihydro-1,2,3,5,6-pentaaza-as-indacene (60.0 mg, 0.15 mmol) was dissolved in DCM, triethylamine (28.0 μL, 0.20 mmol) was added followed by pyridine-3-sulfonyl chloride (32.0 mg, 0.18 mmol) and the reaction stirred at room temperature for 16 hr. The reaction mixture was diluted with DCM, washed with saturated sodium bicarbonate solution and brine, dried over sodium sulfate and concentrated under vacuum to afford 74 mg (91%) of 6-benzenesulfonyl-1-[4-methyl-1-(pyridine-3-sulfonyl)-piperidin-4-yl]-1,6-dihydro-1,2,3,5,6-pentaaza-as-indacene. LCMS (Method H, ESI): RT=3.52 min, m+H=538.3; 1H NMR (400 MHz, DMSO): δ 9.21 (s, 1H), 8.84 (m, 2H), 8.19 (m, 3H), 8.10 (m, 1H), 7.74 (d, 1H), 7.62 (m, 3H), 7.31 (d, 1H), 3.45 (d, 2H), 2.82-2.67 (m, 4H), 2.33 (m, 2H), 1.69 (s, 3H).

Workup

  1. washwashed with saturated sodium bicarbonate solution and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-05821e4c88ca49c49d7885ec34713e8b
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

Loading…