4-Fluorobenzyl bromide → Methyl 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)isonicotinate

HRID 714292Notes

Reaction equation

Br[CH2:2]C1C=CC(F)=CC=1.Br[CH2:11][CH:12]1[CH2:14][CH2:13]1.[O:15]=[C:16]1[NH:20][CH2:19][CH2:18][N:17]1[C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][N:29]=1)[C:24]([O-:26])=[O:25]>>[CH:14]1([CH2:13][N:20]2[CH2:19][CH2:18][N:17]([C:21]3[CH:22]=[C:23]([CH:27]=[CH:28][N:29]=3)[C:24]([O:26][CH3:2])=[O:25])[C:16]2=[O:15])[CH2:12][CH2:11]1

Participants

Reactant 3

HCID 680214-Fluorobenzyl bromide

HCID 81503Bromomethylcyclopropane

HCID 866530512-(2-Oxoimidazolidin-1-yl)isonicotinate

Product 1

HCID 58247757Methyl 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)isonicotinateYield 69%

Procedure

Following the procedure as described in Preparation 17, making variations as required to replace 1-(bromomethyl)-4-fluorobenzene with (bromomethyl)cyclopropane to react with 2-(2-oxoimidazolidin-1-yl)isonicotinate, methyl 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)isonicotinate was obtained as a colorless solid in 69% yield: mp 75-77° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.69 (s, 1H), 8.42 (d, J=5.1 Hz, 1H), 7.35 (d, J=5.1 Hz, 1H), 3.94 (t, J=8.0 Hz, 2H), 3.85 (s, 3H), 3.54 (t, J=8.0 Hz, 2H), 3.06 (d, J=6.9 Hz, 2H), 0.97-0.87 (m, 1H), 0.49-0.43 (m, 2H), 0.22-0.15 (m, 2H); 13C NMR (75 MHz, DMSO-d6) δ 165.8, 156.5, 153.8, 149.1, 138.4, 116.1, 111.4, 53.2, 48.2, 41.7, 41.5, 9.4, 3.6; MS (ES+) m/z 276.3 (M+1).

Workup

customas described in Preparation 17

Sources & evidence

ORD record: ord-362c4e5d8dc6454bbefa0751c5f823be
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187426B2

Reaction notes

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