Chlorosulfonic acid → HCID 51349084, compound

HRID 924880Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[C:12]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[NH:11][C:10](=[O:26])[NH:9]2)=[CH:4][CH:3]=1.Cl[S:28]([OH:31])(=[O:30])=[O:29]>C(Cl)(Cl)Cl>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[C:12]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:11][C:10](=[O:26])[NH:9]2)=[CH:6][C:7]=1[S:28]([OH:31])(=[O:30])=[O:29]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 4-(4-hydroxyphenyl)-5,6-diphenyl-3,4-dihydropyrimidin-2(1H)-one (68 mg, 0.2 mmol) in CHCl3 (1 mL) was added ClSO3H (35 mg, 0.3 mmol). The mixture was heated to 50° C. overnight. The residue was purified by prep-HPLC to give Compound 123 as a white power (6 mg, 7%). 1H NMR (MeOH-d4 500 MHz): δ 7.75 (d, J=7.5 Hz, 1H), 7.38 (d, J=7 Hz, 1H), 7.30 (m, 2H), 7.24 (t, J=1, 5 Hz, 3H), 7.01 (t, J=3.5, 5 Hz, 3H), 6.87 (m, 3H), 5.23 (s, 1H); MS (ESI): m/z 423.0 [M+1]+.

Workup

customThe residue was purified by prep-HPLC

Sources & evidence

ORD record: ord-3810fb5428f340e4bbbce031ef664f0b
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09283229B2

Reaction notes

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