p-Toluenesulfonic acid monohydrate → HCID 86594332, compound

HRID 393826Notes

Reaction equation

HRID 393826 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C@@H:16]3[C@@H:11]([CH2:12][CH2:13][NH:14][CH2:15]3)[CH2:10]2)[CH:5]=[N:6][C:7]=1[Cl:8].O.[CH3:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([OH:28])(=[O:27])=[O:26])=[CH:21][CH:20]=1>>[CH3:18][C:19]1[CH:20]=[CH:21][C:22]([S:25]([OH:28])(=[O:27])=[O:26])=[CH:23][CH:24]=1.[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C@@H:16]3[C@@H:11]([CH2:12][CH2:13][NH:14][CH2:15]3)[CH2:10]2)[CH:5]=[N:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 9813803HCID 9813803, compound

Product 1

HCID 86594332HCID 86594332, compoundYield 67%

Procedure

The product of Example 94B (74 mg, 0.288 mmol) and 4-methylbenzenesulfonic acid monohydrate (55 mg, 0.288 mmol) were combined according to the procedure described in Example 91C to provide the title compound (83 mg, 0.193 mmol, 67% yield). 1H NMR (CH3OH-d4, 300 MHz) δ2.04 (m, 1H), 2.31 (m, 1H), 2.36 (S, 2H), 2.88 (m, 1H), 3.17 (ddd, J=11.8, 7.8, 4.0 Hz, 1H), 3.29 (m, 1H), 3.56 (ddd, J=13.2, 9.1, 4.4 Hz, 1H), 3.64 (dd, J=14.6, 2.0 Hz, 1H) 3.80 (dd, J=7.4, 2.7 Hz, 1H), 3.89 (t, J=7.4 Hz, 1H), 4.41 (dt, J=8.1, 2.4 Hz, 1H), 7.23 (m, 2H), 7.27 (d, J=2.7 Hz, 1H), 7.69 (m, 2H), 7.71 (d, J=2.7 Hz, 1H); MS (DCI/NH3) m/z 258 (M+H)+; Anal. calculated for C11H13Cl2N3.C7H8O3S: C, 50.24; H, 4.92; N, 9.76. Found: C, 50.09; H, 4.94; N, 9.64.

Sources & evidence

ORD record
ord-a117bdeb03c7429a8492940b147de3ab
Source dataset
uspto-grants-2004_10
Patent number
US06809105B2

Reaction notes

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