(1R)-1-{1-[2-(1-methylethyl)-2H-tetrazol-5-yl]-4-piperidinyl}ethanol → 2-[((1S)-1-{1-[2-(1-Methylethyl)-2H-tetrazol-5-yl]-4-piperidinyl}ethyl)oxy]-5-[4-(methylsulfonyl)phenyl]pyrazine

HRID 423710Notes

Reaction equation

HRID 423710 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[CH:13][C:14]([OH:17])=[N:15][CH:16]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH3:18][CH:19]([N:21]1[N:25]=[N:24][C:23]([N:26]2[CH2:31][CH2:30][CH:29]([C@H:32](O)[CH3:33])[CH2:28][CH2:27]2)=[N:22]1)[CH3:20]>>[CH3:20][CH:19]([N:21]1[N:25]=[N:24][C:23]([N:26]2[CH2:31][CH2:30][CH:29]([C@@H:32]([O:17][C:14]3[CH:13]=[N:12][C:11]([C:8]4[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:10][CH:9]=4)=[CH:16][N:15]=3)[CH3:33])[CH2:28][CH2:27]2)=[N:22]1)[CH3:18]

Participants

3

Reactant 2

HCID 66673304(1R)-1-{1-[2-(1-methylethyl)-2H-tetrazol-5-yl]-4-piperidinyl}ethanolHCID 178504683HCID 178504683, compound

Product 1

HCID 249955862-[((1S)-1-{1-[2-(1-Methylethyl)-2H-tetrazol-5-yl]-4-piperidinyl}ethyl)oxy]-5-[4-(methylsulfonyl)phenyl]pyrazineYield 58%

Procedure

The title compound (145 mg, 58%) was prepared from 5-[4-(methylsulfonyl)phenyl]-2-pyrazinol (and tautomers thereof) (prepared as in Example 145, Steps 1-2, 125 mg, 0.5 m mol) and (1R)-1-{1-[2-(1-methylethyl)-2H-tetrazol-5-yl]-4-piperidinyl}ethanol (prepared as in Example 190, Step 3, 120 mg, 0.5 mmol) in a manner similar to Example 190, Step 4. Enantiomeric excess was not determined. 1H NMR (400 MHz, DMSO-d6): 8.91 (d, 1H, J=1.4 Hz), 8.41 (d, 1H, J=1.4 Hz), 8.34-8.26 (m, 2H), 8.07-7.99 (m, 2H), 5.13 (quint, 1H, J=6.2 Hz), 4.87 (septet, 1H, J=6.7 Hz), 4.06-3.91 (m, 2H), 3.26 (s, 3H), 2.95-2.78 (m, 2H), 1.96-1.71 (m, 3H), 1.49 (d, 6H, J=6.7 Hz), 1.45-1.35 (m, 2H), 1.32 (d, 3H, J=6.2 Hz); LRMS (ESI), m/z 472 (M+H).

Sources & evidence

ORD record
ord-b280a8986520485ca4afc5ae6d5128a8
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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