Triethylamine → HCID 53988546, compound

HRID 1432993Notes

Reaction equation

Cl.[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([CH2:13][N:14]3[CH2:19][CH2:18][NH:17][C@@H:16]([CH3:20])[C:15]3=[O:21])=[CH:10][CH:11]=2)[N:6]=[CH:5][CH:4]=1.[Br:22][C:23]1[CH:24]=[C:25](/[CH:28]=[CH:29]/[C:30](O)=[O:31])[S:26][CH:27]=1.BrC1C=C(C=O)SC=1.C(N(CC)CC)C>CN(C=O)C>[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([CH2:13][N:14]3[CH2:19][CH2:18][N:17]([C:30](=[O:31])[CH:29]=[CH:28][C:25]4[S:26][CH:27]=[C:23]([Br:22])[CH:24]=4)[C@@H:16]([CH3:20])[C:15]3=[O:21])=[CH:10][CH:11]=2)[N:6]=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 50 °C

Procedure

(S)-1-(4-chloroquinolin-7-ylmethyl)-3-methylpiperazin-2-one hydrochloride (0.35 g, 1.4 mmol), EXAMPLE 91, is treated with DMF (20 mL), 3-(4-bromothiophen-2-yl)-(E)-acrylic acid (0.32 g, 1.4 mmol), prepared according to EXAMPLE 26, using 4-bromothiophene-2-carboxaldehyde, triethyl amine (0.21 ml, 1.4 mmol) and 2-(1H-benzotriazol-1-yl)1,1,3,3-tertamethyluronium tetrafluoroborate (0.45 g, 1.4 mmol) and heated to 50° C. for 5 minutes. The reaction mixture is stirred at ambient temperature for 16 h then partitioned between ethyl acetate and water. The organic layer is concentrated and the residue is chromatographed (5% methanol/methylene chloride) to give crude title compound (0.5 g, 0.9 mmol). MS m/z: [M+H]+=504. 1H NMR (CDCl3, 300 MHz) δ8.9 (d, 1H), 8.2-8.3 (m, 2H), 8.0 (s, 1H), 7.7-7.8 (m, 1H), 7.4 (s, 1H), 7.3-7.4 (m, 1H), 6.7-6.8 (m, 1H), 6.6 (d, 1H), 5.1-5.2 (m, 1H), 4.6-4.7 (m, 2H), 3.4-3.6 (m, 2H), 3.0-3.3 (m, 2H), 1.5 (d, 3H).

Workup

customprepared
customthen partitioned between ethyl acetate and water
concentrationThe organic layer is concentrated
customthe residue is chromatographed (5% methanol/methylene chloride)

Sources & evidence

ORD record: ord-6aa2a95af6ea4cd0904fd083853e4f28
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612075B2

Reaction notes

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