Hexane → HCID 10166738, compound

HRID 1278776Notes

Reaction equation

HRID 1278776 reaction equation
[NH2:1][CH2:2][C@@H:3]([C:5]1[CH:6]=[CH:7][C:8]([OH:16])=[C:9]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:10]=1)[OH:4].[CH3:17][N:18]1[CH2:23][CH2:22][N:21]([S:24]([C:27]2[CH:32]=[CH:31][C:30]([N:33]3[CH2:38][CH2:37][C:36](=O)[CH2:35][CH2:34]3)=[CH:29][CH:28]=2)(=[O:26])=[O:25])[CH2:20][CH2:19]1.CCCCCC>O>[OH:16][C:8]1[CH:7]=[CH:6][C:5]([C@@H:3]([OH:4])[CH2:2][NH:1][CH:36]2[CH2:35][CH2:34][N:33]([C:30]3[CH:29]=[CH:28][C:27]([S:24]([N:21]4[CH2:22][CH2:23][N:18]([CH3:17])[CH2:19][CH2:20]4)(=[O:26])=[O:25])=[CH:32][CH:31]=3)[CH2:38][CH2:37]2)=[CH:10][C:9]=1[NH:11][S:12]([CH3:15])(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 8058HexaneHCID 12047933(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamideHCID 22713399HCID 22713399, compound

Product 1

HCID 10166738HCID 10166738, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared from N-{5-[(1R)-2-amino-1-hydroxyethyl]-2-hydroxyphenyl}methanesulfonamide, and 1-{4-[(4-methyl-1-piperazinyl)sulfonyl]phenyl}-4-piperidinone in substantially the same manner, as described in Example 50. The product was obtained as a brown solid; mp: 89-91° C.; 1H NMR (400 MHz, DMSO-d6): δ 1.53-1.65 (m, 2H), 2.06-2.16 (m, 2H), 2.82-2.89 (m, 2H), 2.94 (s, 3H), 3.09-3.13 (m, 2H), 3.70 (brs, 2H), 4.01-4.05 (m, 2H), 4.76-4.79 (d, 2H), 6.11 (brs, 1H), 6.88-6.90 (d, 2H), 7.06-7.13 (m, 4H), 7.25 (s, 1H), 7.52-7.55 (d, 2H), 8.60 (brs, 1H); 8.58 (brs, 1H); 8.75 (s, 1H), 9.64 (brs, 1H), 10.00 (s, 1H); MS m/z 568 (M+H)+; Analysis for C25H37N5O6S2×0.4 hexane×0.52 H2O Calc'd: C, 42.07; H, 4.93; N, 7.34; Found: C, 42.27; H, 4.60; N, 6.70.

Workup

  1. customThe product was obtained as a brown solid

Sources & evidence

ORD record
ord-feb2ba3bc6364685a391ddc3fc335196
Source dataset
uspto-grants-2002_09
Patent number
US06444685B1

Reaction notes

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