3-tert-Butyl-4-methoxy-benzenesulfonyl chloride → (7R,8aS)-2-[(6-tert-butylpyridin-2-yl)sulfonyl]-7-{[5-(prop-1-en-2-yl)-pyrazin-2-yl]oxy}octahydropyrrolo[1,2-a]pyrazine

HRID 240452Notes

Reaction equation

HRID 240452 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:20]([C:24]1[N:29]=[C:28]([S:30](Cl)(=[O:32])=[O:31])[CH:27]=[CH:26][CH:25]=1)([CH3:23])([CH3:22])[CH3:21].C(C1C=C(S(Cl)(=O)=O)C=CC=1OC)(C)(C)C>>[C:20]([C:24]1[N:29]=[C:28]([S:30]([N:17]2[CH2:16][CH2:15][N:14]3[CH2:19][C@H:11]([O:10][C:7]4[CH:6]=[N:5][C:4]([C:1]([CH3:2])=[CH2:3])=[CH:9][N:8]=4)[CH2:12][C@H:13]3[CH2:18]2)(=[O:32])=[O:31])[CH:27]=[CH:26][CH:25]=1)([CH3:23])([CH3:21])[CH3:22]

Participants

4

Reactant 3

HCID 110652633-tert-Butyl-4-methoxy-benzenesulfonyl chlorideHCID 86680449(7R,8aS)-7-[(5-cyclopropylpyrazin-2-yl)oxy]octahydropyrrolo[1,2-a]pyrazineHCID 866804616-Tert-butylpyridine-2-sulfonyl chloride

Product 1

HCID 86680460(7R,8aS)-2-[(6-tert-butylpyridin-2-yl)sulfonyl]-7-{[5-(prop-1-en-2-yl)-pyrazin-2-yl]oxy}octahydropyrrolo[1,2-a]pyrazine

Procedure

The title compound was prepared according to the procedure described in Example 57, substituting the product from Example 202C (82 mg, 0.28 mmol) for the product from Example 27B, and substituting the product from Example 58B for 3-tert-butyl-4-methoxybenzene-1-sulfonyl chloride. The title compound was obtained as a colorless solid (79 mg, 62%). 1H NMR (300 MHz, CDCl3) δ ppm 1.39 (s, 9H), 1.78-2.06 (m, 2H), 2.17 (s, 3H), 2.31-2.49 (m, 2H), 2.50-2.62 (m, 1H), 2.61-2.74 (m, 1H), 2.91-3.06 (m, 2H), 3.69 (dd, J=9.92, 6.74 Hz, 1H), 3.85-3.96 (m, 1H), 4.02-4.13 (m, 1H), 5.22 (t, J=1.59 Hz, 1H), 5.32-5.42 (m, 1H), 5.77-5.81 (m, J=1.59 Hz, 1H), 7.51 (dd, J=7.54, 1.19 Hz, 1H), 7.71-7.84 (m, 2H), 8.15 (d, J=1.59 Hz, 1H), 8.20 (d, J=1.19 Hz, 1H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-23cceb29458144f0b1fe5cbf6a6081da
Source dataset
uspto-grants-2014_02
Patent number
US08648074B2

Reaction notes

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