Triethylamine → HCID 11375343, compound

HRID 561276Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][S:8]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([NH:21][C:22](=[O:29])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH2:3][CH2:2]1.CCN(CC)CC.[N:37]([CH:40]([CH3:42])[CH3:41])=[C:38]=[O:39]>C(Cl)Cl>[CH:40]([NH:37][C:38]([N:1]1[CH2:6][CH2:5][CH:4]([NH:7][S:8]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([NH:21][C:22](=[O:29])[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH2:3][CH2:2]1)=[O:39])([CH3:42])[CH3:41]

Participants

Conditions

Temperature: 25 °C

Procedure

To a 25° C. solution of N-[4-(piperidin-4-yl sulfamoyl)-naphthalen-1-yl]-benzamide (C-1) in CH2Cl2 was added Et3N followed by 2-isocyanato-propane. The reaction mixture was stirred at 25° C. overnight. Aqueous work-up followed by purification using reverse phase HPLC provided the title compound. 1H NMR (300 MHz, MeOD) δ 8.74 (d, 1H), 8.29 (d, 1H), 8.17 (d, 1H), 8.07 (s, 1H), 8.05 (s, 1H), 7.81 (d, 1H), 7.63 (m, 5H), 3.75 (m, 3H), 3.21 (m, 1H), 2.68 (t, 2H), 1.51 (m, 2H), 1.26 (m, 2H), 1.05 (d, 6H); LC/MS (M+H)+ m/z 495.

Workup

customAqueous work-up followed by purification

Sources & evidence

ORD record: ord-7968daa2fdae4ae28f677a355a61776f
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063222B2

Reaction notes

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