Dimethyl Sulfoxide → HCID 136352014, compound

HRID 2213681Notes

Reaction equation

[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6]2.[C:13]([C:16]1[NH:17][CH:18]=[CH:19][CH:20]=1)(=O)[CH3:14].[NH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.[CH3:27]S(C)=O>>[NH:17]1[CH:18]=[CH:19][CH:20]=[C:16]1[C:13](=[N:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]2=[C:22]([C:23]1[NH:21][CH:26]=[CH:25][CH:24]=1)[CH3:27])[CH3:14]

Participants

Reactant 4

HCID 679Dimethyl Sulfoxide

HCID 8082Piperidine

HCID 140792-Acetylpyrrole

HCID 179825555-(Aminomethyl)indolin-2-one

Product 1

HCID 136352014HCID 136352014, compound

Conditions

Temperature: 160 °C

Procedure

5-Aminomethylindolin-2-one (160 mg, 1 mmol), 2-acetylpyrrole (190 mg, 1.74 mmol) and piperidine (0.4 mL) were mixed together in a microwave reaction vessel and heated to 160° C. for 8 minutes in a microwave reactor. The resulting black-colored solid was dissolved in DMSO and purified by reverse phase HPLC (acetonitrile/water) to afford 5-((1-pyrrol-2-yl)ethylidene)aminomethyl-3-[1-(pyrrol-2-yl)ethylidene]indolin-2-one; (20 mg), as a trifluoroacetate salt; 1H NMR (400 MHz, DMSO) δ 2.74 (s, 3H) 2.76 (s, 3H), 4.90 (d, 2H), 6.34 (m, 1H), 6.50 (m, 1H), 6.92 (d, 1H), 7.08 (m, 1H), 7.24 (d, 1H), 7.42 (s, 1H), 7.60 (m, 2H), 7.78 (s, 1H), 11.20 (s, 1H), 11.28 (brs, 1H) ppm.

Workup

custompurified by reverse phase HPLC (acetonitrile/water)

Sources & evidence

ORD record: ord-be594f5154214c088b167f18668dc53a
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07105563B2

Reaction notes

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