1-Phenethylamine, (-)- → HCID 69701911, compound

HRID 2415696Notes

Reaction equation

[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][N:7]2[C:11]([C:22]3[N:23](S(C)(=O)=O)[CH2:24][N:25]=[CH:26][CH:27]=3)=[C:12]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[C:13](=[O:14])[N:6]12)=[O:4].[CH3:32][C@H:33]([NH2:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C1(C)C=CC=CC=1.Cl>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][N:7]2[C:11]([C:22]3[CH:27]=[CH:26][N:25]=[C:24]([NH:40][C@H:33]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[CH3:32])[N:23]=3)=[C:12]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[C:13](=[O:14])[N:6]12)=[O:4]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-(4fluorophenyl)-1-(3-methanesulfonyl-pyrimidin-4-yl)-3-oxo-5,6, 7, 8-tetrahydro-3H-pyrazolo[1,2-a]pyridazine-5-carboxylic acid methyl ester, 21, (0.10 g, 0.22 mmol) in toluene (1.4 mL) is added (S)-(−)-α-methylbenzylamine (1.4 mL, 1.12 mmol). The reaction solution is heated to 100° C. for 4 hours after which the reaction is cooled and diluted with 1 N HCl. The resulting solution is extracted with ethyl acetate (3×25 mL), the organic layers are combined, dried, and concentrated in vacuo to afford 0.071 g (66% yield) of the desired product as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 8.22 (ddd, J=11.4, 5.1, 2.1 Hz, 1 H), 7.22-7.37 (m, 7 H), 6.97 (dt, J=8.7, 2.1 Hz, 2 H), 6.41 (ddd, J=15.6, 5.1, 2.1 Hz, 1H), 5.72-5.83 (m, 1 H), 5.2 (br s, 2 H), 5.52-5.62 (m, 1 H), 3.77 (s, 3 H), 3.47 (d, J=2.7 Hz, 1 H), 2.47-2.51 (m, 2 H), 200 (br s, 1 H), 1.41 (d, J=6.6 Hz, 3 H); APCI/MS: 487 (M+H).

Workup

temperatureis cooled
extractionThe resulting solution is extracted with ethyl acetate (3×25 mL)
customdried
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-18b6935053d843fe8593929d29647698
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06821971B2

Reaction notes

Loading…