3-Ethylaniline → HCID 67156717, compound

HRID 549287Notes

Reaction equation

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

Participants

Reactant 2

HCID 114753-Ethylaniline

HCID 86591054HCID 86591054, compound

Product 1

HCID 67156717HCID 67156717, compoundYield 76.5%

Procedure

Prepared from tert-butyl 4-[3-(chlorosulfonyl)thieno[3,2-c]pyridin-4-yl]piperazine-1-carboxylate (90.0 mg, 0.215 mmol) and 3-ethylaniline (33.9 mg, 0.28 mmol) to give the title compound as an off-white solid (82.7 mg, 76%). 1H NMR (400 MHz, CDCl3) δ 1.03 (t, J=7.5 Hz, 3H), 1.48 (s, 9H), 2.47 (q, J=7.7 Hz, 2H), 3.00-3.53 (m, 6H), 4.02-4.44 (m, 2H), 6.66 (d, J=8.0 Hz, 1H), 6.75 (s, 1H), 6.66 (d, J=8.0 Hz, 1H), 7.02 (t, J=7.8 Hz, 1H), 7.67 (d, J=5.5 Hz, 1H), 8.24 (s, 1H), 8.39 (d, J=5.5 Hz, 1H), 9.80 (s, 1H). MS (ESI+) m/z 503.2 (M+H)+. HPLC 97%, RT: 3.93 min (5-99% MeCN over 3 min).

Sources & evidence

ORD record: ord-331e627d674f4fa6a4e5ef7bd4b51386
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07943639B2

Reaction notes

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