9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one → HCID 68229162, compound

HRID 1853786Notes

Reaction equation

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

Participants

Reactant 2

HCID 674491399-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one

HCID 86689492HCID 86689492, compound

Product 1

HCID 68229162HCID 68229162, compoundYield 20%

Procedure

Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (110 mg, 0.31 mmol) was reacted with 4-({4-[(tert-butoxycarbonylamino)methyl]piperidin-1-yl}methyl)phenylboronic acid (80 mg, 0.26 mol) to afford the desired product (25 mg, 20%) as a yellow glass: 1H NMR (500 MHz, CD3OD) δ 7.69-7.66 (m, 2H), 7.57-7.54 (m, 2H), 7.41-7.38 (m, 3H), 5.96-5.95 (m, 1H), 4.48-4.44 (m, 2H), 3.75 (s, 3H), 3.70-3.64 (m, 2H), 3.27-2.91 (m, 4H), 2.25-1.95 (m, 2H), 1.57 (s, 1H), 1.52-1.42 (m, 10H); ESI MS m/z 534 [C30H35N3O4S+H]+; HPLC 97.6% (AUC), tR=14.10 min.

Sources & evidence

ORD record: ord-bca868277a804af08207d35371487774
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962648B2

Reaction notes

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