Triethylamine → HCID 178480388, compound

HRID 929109Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[C:3]=1[C:9]1[NH:20][C:19]2[C:11](=[CH:12][C:13]3[CH2:14][N:15]([CH:22]4[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]4)[C:16](=[O:21])[C:17]=3[CH:18]=2)[N:10]=1.[NH2:29][CH2:30][CH2:31][NH:32][S:33]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[Br:42])(=[O:35])=[O:34].CCN(CC)CC>CCO>[Br:42][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=1[S:33]([NH:32][CH2:31][CH2:30][NH:29][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[C:3]=1[C:9]1[NH:20][C:19]2[C:11]([N:10]=1)=[CH:12][C:13]1[CH2:14][N:15]([CH:22]3[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]3)[C:16](=[O:21])[C:17]=1[CH:18]=2)(=[O:35])=[O:34]

Participants

Conditions

Temperature: 95 °C

Procedure

To a solution of 2-(4-chloro-2-oxo-1,2-dihydro-pyridin-3-yl)-6-(1-methyl-piperidin-4-yl)-6,7-dihydro-3H-1,3,6-triaza-s-indacen-5-one (40 mg, 0.1 mmol) and N-(2-amino-ethyl)-2-bromo-benzenesulfonamide (56 mg, 0.20 mmol) in EtOH (4 mL) was added Et3N (500 μL, 3.6 mmol) and the reaction was heated at 95° C. for 16 h. The solvent was evaporated in vacuo and the residue was purified by flash chromatography with CH2Cl2/MeOH/28% aqueous NH4OH (100:10:1) afforded the title compound (7.3 mg, 11%). 1H NMR (DMSO-d6) δ 1.70 (m, 2H), 1.85 (m, 2H), 2.15 (m, 2H), 2.29 (s, 3H, CH3), 2.96 (m, 2H), 3.19 (m, 1H), 3.50 (m, 2H), 4.05 (m, 1H), 4.48 (s, 1H), 6.05 (d, J=7 Hz, 1H), 7.32 (br s, 1H), 7.38-7.50 (1.5H), 7.62-7.70 (1.5H), 7.82 (s, 0.5H), 7.87 (s, 0.5H), 7.96-7.99 (2H), 8.20) br S, 1H, NH), 11.02 (br s, 1H, NH), 11.26 (br s, 1H, NH); ESI-MS m/z 640.5 (MH+).

Workup

customThe solvent was evaporated in vacuo
customthe residue was purified by flash chromatography with CH2Cl2/MeOH/28% aqueous NH4OH (100:10:1)

Sources & evidence

ORD record: ord-6b8831745080496d942528ce7f039f81
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290503B2

Reaction notes

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