Ethylenediamine → 3-(2,5-Dihydro-1H-imidazol-2-ylmethyl)-1-methanesulfonyl-1H-pyrrolo[2,3-b]pyridine

HRID 489735Notes

Reaction equation

[CH3:1][S:2]([N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([CH2:14][C:15]#[N:16])=[CH:6]1)(=[O:4])=[O:3].[CH2:17](N)[CH2:18][NH2:19]>C(=S)=S>[OH-:3].[NH4+:5].[NH:16]1[CH2:17][CH:18]=[N:19][CH:15]1[CH2:14][C:7]1[C:8]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[N:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH:6]=1

Participants

Conditions

Temperature: 140 °C

Procedure

Carbon disulfide (2 drops) and (1-Methanesulfonyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-acetonitrile (4) (81 mg, 0.34 mmol) was added sequentially in this order to ethylenediamine (2 ml). The reaction was heated at 140° C. for 30 minutes and concentrated under reduced pressure. The residue was chromatographed over silica gel eluting with 92:8:1 ethyl acetate:methanol:ammonium hydroxide to obtain 3-(2,5-Dihydro-1H-imidazol-2-ylmethyl)-1-methanesulfonyl-1H-pyrrolo[2,3-b]pyridine (50 mg, 53%). 1H NMR (DMSO-d6) δ: 3.40 (4H, s), 3.70 (3H, s), 7.37 (1H, dd, J=4.7 Hz, 7.9 Hz), 7.64 (1H, s), 8.11 (1H, dd, J=1.5 Hz, 7.9 Hz), 8.42 (1H, dd, J=1.5 Hz, 4.7 Hz); M+H 279.

Workup

concentrationconcentrated under reduced pressure
customThe residue was chromatographed over silica gel eluting with 92:8:1 ethyl acetate

Sources & evidence

ORD record: ord-6e0bf85e8c084a688563e834b0ddcb1c
Source dataset: uspto-grants-2005_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06979696B2

Reaction notes

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