p-Toluenesulfonic acid monohydrate → HCID 86584389, compound

HRID 393825Notes

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

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrate

HCID 9856458HCID 9856458, compound

Product 1

HCID 86584389HCID 86584389, compoundYield 77.1%

Procedure

The product of Example 93B (45.0 mg, 0.175 mmol) and 4-methylbenzenesulfonic acid monohydrate (33.3 mg, 0.175 mmol) were processed according to the procedure described in Example 91C to provide the title compound (58 mg, 0.135 mmol, 77% yield). 1H NMR (CH3OH-d4, 300 MHz) δ2.04 (m, 1H), 2.30 (m, 1H), 2.39 (s, 3H), 2.89 (m, 1H), 3.16 (ddd, J=12.2, 7.4, 4.1 Hz, 1H), 3.28 (m, 1H), 3.57 (ddd, J=12.9, 8.8, 4.1 Hz, 1H), 3.64 (dd, J=14.6, 2.0 Hz, 1H), 3.79 (dd, J=7.5, 2.7 Hz, 1H), 3.90 (t, J=7.5 Hz, 1H), 4.41 (dt, J=8.1, 2.4 Hz, 1H), 7.22 (m, 2H), 7.27 (d, J=2.7 Hz, 1H), 7.70 (m, 3H); MS (DCI/NH3) m/z 258 (M+H)+; Anal. calculated for C11H13Cl2N3.C7H8O3S: C, 50.24; H, 4.92; N, 9.76. Found: C, 50.14; H, 4.88; N, 9.67.

Sources & evidence

ORD record: ord-556754a1def846b9bafb8bffd8345198
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06809105B2

Reaction notes

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