2-Morpholinoethylamine → HCID 20767803, compound

HRID 1825237Notes

Reaction equation

[CH3:1][C:2]1[S:6][C:5]2[CH:7]=[C:8]([O:11][C:12]3[CH:17]=[CH:16][N:15]=[C:14]4[CH:18]=[C:19]([CH3:21])[S:20][C:13]=34)[CH:9]=[CH:10][C:4]=2[C:3]=1[C:22](Cl)=[O:23].[N:25]1([CH2:31][CH2:32][NH2:33])[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>>[N:25]1([CH2:31][CH2:32][NH:33][C:22]([C:3]2[C:4]3[CH:10]=[CH:9][C:8]([O:11][C:12]4[CH:17]=[CH:16][N:15]=[C:14]5[CH:18]=[C:19]([CH3:21])[S:20][C:13]=45)=[CH:7][C:5]=3[S:6][C:2]=2[CH3:1])=[O:23])[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1

Participants

Reactant 2

HCID 4082852-Morpholinoethylamine

HCID 22143640HCID 22143640, compound

Product 1

HCID 20767803HCID 20767803, compoundYield 75%

Procedure

This material was prepared from 2-methyl-6-(2-methylthieno[3,2-b]pyridin-7-yloxy)benzo[b]thiophene-3-carbonyl chloride 139d (112 mg, 0.3 mmole) and 2-(morpholin-4-yl)ethylamine (157 mg, 1.2 mmole) in a similar manner as that described for example 108 to give a yellow solid (105 mg, 75%). 1H NMR (DMSO-d6) δ 8.44 (1H, d, J=5.5 Hz), 8.29 (1H, t, J=4.8 Hz), 7.94 (1H, d, J=8.7 Hz), 7.92 (1H, d, J=2.3 Hz), 7.31 (1H, s), 7.30 (1H, dd, J=2.3, 8.7 Hz), 6.60 (1H, d, J=5.5 Hz), 3.60 (4H, t, J=4.2 Hz), 3.45 (2H, dt, J=4.8, 6.2 Hz), 2.64 (3H, s), 2.62 (3H, s), 2.55–2.41 (6H, m).

Sources & evidence

ORD record: ord-dbb372331fc34292b26578d6c1259ee8
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07045528B2

Reaction notes

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