HCID 68709356, compound → HCID 24786072, compound

HRID 2239354Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([C:13]([O:15]C)=O)=[C:10](/[N:17]=[CH:18]/[N:19]([CH3:21])C)[CH:9]=2)=[CH:4][CH:3]=1.[N:22]12[CH2:29][CH2:28][CH:25]([CH2:26][CH2:27]1)[C@@H:24]([O:30][C:31]1[CH:32]=[C:33](CN)[CH:34]=[CH:35][CH:36]=1)[CH2:23]2>CO>[N:22]12[CH2:29][CH2:28][CH:25]([CH2:26][CH2:27]1)[C@@H:24]([O:30][C:31]1[CH:36]=[C:35]([CH:34]=[CH:33][CH:32]=1)[CH2:21][N:19]1[C:13](=[O:15])[C:11]3[S:12][C:8]([C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=4)=[CH:9][C:10]=3[N:17]=[CH:18]1)[CH2:23]2

Participants

Conditions

Temperature: 120 °C

Procedure

Methyl 5-(4-chlorophenyl)-3-{[(1E)-(dimethylamino)methylene]amino}thiophene-2-carboxylate (177 mg, 0.548 mmol) and 1-{3-[(3R)-1-azabicyclo[2.2.2]oct-3-yloxy]phenyl}methanamine (140 mg, 0.603 mmol) were dissolved in MeOH (2 ml). The reaction was heated in a microwave at 120° C. for 30 minutes. The solvent was evaporated in vacuo. Purification by flash silica gel chromatography using a 40 g Biotage column with 100% EtOAc/MeOH/TEA 100:10:1 yielded the title compound as a white solid. Yield: 0.175 g (67%). 1H NMR (400 MHz, CDCl3) δ 8.09 (s, 1H), 7.56 (m, 2H), 7.40 (s, 1H), 7.37 (m, 2H), 7.22 (t, 1H, J=7.9 Hz), 6.88 (d, 1H, J=7.9 Hz), 6.86 (m, 1H), 6.75 (dd, 1H, J=8.1 Hz, J=2.1 Hz), 5.15 (s, 2H), 4.33 (m, 1H), 3.24 (m, 1H), 2.97-2.88 (m, 1H), 2.86-2.69 (m, 4H), 2.08 (m, 1H), 1.99-1.88 (m, 1H), 1.70 (m, 1H), 1.57-1.47 (m, 1H), 1.34 (m, 1H). 13C NMR (100 MHz, CDCl3) δ 158.3, 157.7, 157.1, 151.4, 148.2, 137.5, 135.7, 131.7, 130.4, 129.6, 127.8, 123.2, 121.0, 120.4, 115.8, 115.2, 73.6, 55.8, 49.5, 47.5, 46.8, 25.3, 24.6, 19.4. MS (ESI+) 478.00 (M+1H+).

Workup

customThe solvent was evaporated in vacuo
customPurification by flash silica gel chromatography

Sources & evidence

ORD record: ord-3c686ff4a87b408c89015edc250a0d31
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723331B2

Reaction notes

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