HCID 21114501, compound → HCID 58890823, compound

HRID 493724Notes

Reaction equation

[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N:9]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]2)=[CH:4][C:3]=1[CH2:16][C:17]([NH2:19])=[O:18].[NH:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]([C:29](=O)[C:30]([O-])=[O:31])=[CH:21]1.C(O[K])(C)(C)C>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N:9]2[CH2:10][CH2:11][N:12]([CH3:15])[CH2:13][CH2:14]2)=[CH:4][C:3]=1[C:16]1[C:17](=[O:18])[NH:19][C:30](=[O:31])[C:29]=1[C:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[NH:20][CH:21]=1

Participants

Conditions

Temperature: 35 °C

Procedure

2-[2-Chloro-3-methyl-5-(4-methyl-piperazin-1-yl)-phenyl]-acetamide (211 mg, 0.75 mmol) and 3-indoleglyoxylate (270 mg, 1.35 mmol) are dissolved in THF (5 mL). A solution of 1.0 M tert-BuOK in THF (2.98 mL, 4 eq) is added and the mixture is stirred at 35° C. overnight. The reaction is diluted with AcOEt (20 mL) and washed with H2O (20 mL) and brine (10 mL). The organic phase is dried over Na2SO4 and the solvent is evaporated. The residue is purified by FCC (AcOEt/AcOH/H2O 7:1:1) to afford the title compound in the form of its acetate salt. 1H NMR (DMSO, 400 MHz) δ 2.16 (s, 3H), 2.31 (s, 3H), 2.32-2.38 (m, 4H), 2.97-3.10 (m, 4H), 6.61 (d, J=8.0 Hz, 1H), 6.71-6.77 (m, 2H), 7.04 (d, J=2.8 Hz, 1H), 7.08 (dd, J=7.4, 7.2 Hz, 1H), 7.41 (d, J=8.2 Hz, 1H), 7.98 (d, J=1.5 Hz, 1H), 11.05 (br s, 1H), 11.90 (br s, 1H); ES-MS: 435 [M+H]+.

Workup

washwashed with H2O (20 mL) and brine (10 mL)
dry with materialThe organic phase is dried over Na2SO4
customthe solvent is evaporated
customThe residue is purified by FCC (AcOEt/AcOH/H2O 7:1:1)

Sources & evidence

ORD record: ord-6f7ca518574f4f54af8981d687c98b18
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07534808B2

Reaction notes

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