Triethylamine → 1-(3-{[(7R,8aS)-7-[(5-cyclopropylpyrazin-2-yl)oxy]hexahydropyrrolo[1,2-a]-pyrazin-2(1H)-yl]sulfonyl}phenyl)ethanone

HRID 240442Notes

Reaction equation

HRID 240442 reaction equation
[CH:1]1([C:4]2[N:5]=[CH:6][C:7]([O:10][C@H:11]3[CH2:19][N:14]4[CH2:15][CH2:16][NH:17][CH2:18][C@@H:13]4[CH2:12]3)=[N:8][CH:9]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[C:27]([C:30]1[CH:31]=[C:32]([S:36](Cl)(=[O:38])=[O:37])[CH:33]=[CH:34][CH:35]=1)(=[O:29])[CH3:28]>ClCCl>[CH:1]1([C:4]2[N:5]=[CH:6][C:7]([O:10][C@H:11]3[CH2:19][N:14]4[CH2:15][CH2:16][N:17]([S:36]([C:32]5[CH:31]=[C:30]([C:27](=[O:29])[CH3:28])[CH:35]=[CH:34][CH:33]=5)(=[O:38])=[O:37])[CH2:18][C@@H:13]4[CH2:12]3)=[N:8][CH:9]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27562603-Acetylbenzenesulfonyl chlorideHCID 86680449(7R,8aS)-7-[(5-cyclopropylpyrazin-2-yl)oxy]octahydropyrrolo[1,2-a]pyrazine

Product 1

HCID 715441021-(3-{[(7R,8aS)-7-[(5-cyclopropylpyrazin-2-yl)oxy]hexahydropyrrolo[1,2-a]-pyrazin-2(1H)-yl]sulfonyl}phenyl)ethanoneYield 83.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To (7R,8aS)-7-[(5-cyclopropylpyrazin-2-yl)oxy]octahydropyrrolo[1,2-a]pyrazine (1 mmol, Example 27B) and triethylamine (1.5 mmol) in dichloromethane (6 mL) was added 3-acetylbenzene-1-sulfonyl chloride (1.1 mmol) in dichloromethane (2 mL). The mixture was stirred at room temperature for 18 hours. The mixture was concentrated, and the residue was purified by chromatography on silica gel (ethyl acetate) to give the title compound (370 mg) as a solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.81 (m, 2H), 0.91 (m, 2H), 1.75 (m, 1H), 1.89 (m, 1H), 2.06 (m, 2H), 2.19 (m, 2H), 2.30 (m, 3H), 3.67 (s, 2H), 2.97 (m, 1H), 3.54 (m, 1H), 3.65 (m, 1H), 3.80 (m, 1H), 5.19 (m, 1H), 7.83 (m, 1H), 8.00 (m, 1H), 8.15 (m, 3H), 8.30 (m, 1H); MS (ESI) m/z 444 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by chromatography on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-072b4ad1a2a3454fab3ea07ce0e30613
Source dataset
uspto-grants-2014_02
Patent number
US08648074B2

Reaction notes

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