187154-69-4 → HCID 69141782, compound

HRID 1794128Notes

Reaction equation

HRID 1794128 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH2:4][OH:5].[N:11]1[S:12][N:13]=[C:14]2[CH:19]=[C:18]([CH2:20]Cl)[CH:17]=[CH:16][C:15]=12.Cl[C:23]([N:25]1[C@H:30]([CH3:31])[CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27][C@@H:26]1[CH3:39])=[O:24]>>[CH3:39][C@H:26]1[CH2:27][NH:28][CH2:29][C@@H:30]([CH3:31])[N:25]1[C:23]([O:5][CH2:4][C:3]1[CH:6]=[C:7]([O:10][CH2:20][C:18]2[CH:17]=[CH:16][C:15]3=[N:11][S:12][N:13]=[C:14]3[CH:19]=2)[CH:8]=[CH:9][C:2]=1[F:1])=[O:24]

Participants

4

Reactant 3

HCID 11084549187154-69-4HCID 691416144-Fluoro-3-(hydroxymethyl)phenolHCID 86585999rel-1,1-Dimethylethyl (3R,5S)-4-(chlorocarbonyl)-3,5-dimethyl-1-piperazinecarboxylate

Product 1

HCID 69141782HCID 69141782, compound

Procedure

5-(5-[2,1,3]Benzothiadiazolylmethyl)oxy-2-fluorobenzyl cis-2,6-dimethylpiperazine-1-carboxylate was prepared from 2-fluoro-5-hydroxybenzyl alcohol, 5-[2,1,3]benzothiadiazolylmethyl chloride and 1-chlorocarbonyl-cis-2,6-dimethyl-4-tert-butoxycarbonylpiperazine according to the procedures described for Examples 121 and 54 to give the product as a yellow oil: δH (400 MHz, DMSO-d6) 1.25 (6H, d, J 7.0 Hz), 2.78–2.95 (4H, m), 4.10 (2H, br), 5.20 (2H, s), 5.22 (2H, s), 6.90–7.08 (3H, m), 7.65 (1H, m) and 8.03 (2H, m), NH not observed; HPLC (XTERRA, 50/80%, 220 nm) 90.7% (4.84 min).

Sources & evidence

ORD record
ord-6c634d67cac142a8a0aff0042bc2112a
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

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