1-Aminohydantoin → 1-[(E)-1-[3-[(7-fluoroquinolin-6-yl)methyl]triazolo[4,5-b]pyrazin-5-yl]ethylideneamino]imidazolidine-2,4-dione

HRID 456171Notes

Reaction equation

HRID 456171 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[CH2:12][N:13]1[C:21]2[C:16](=[N:17][CH:18]=[C:19]([C:22](=O)[CH3:23])[N:20]=2)[N:15]=[N:14]1.[NH2:25][N:26]1[CH2:30][C:29](=[O:31])[NH:28][C:27]1=[O:32]>>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[CH2:12][N:13]1[C:21]2[C:16](=[N:17][CH:18]=[C:19](/[C:22](=[N:25]/[N:26]3[CH2:30][C:29](=[O:31])[NH:28][C:27]3=[O:32])/[CH3:23])[N:20]=2)[N:15]=[N:14]1

Participants

3

Reactant 2

HCID 728231-AminohydantoinHCID 581905781-[3-(7-Fluoro-quinolin-6-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl]-ethanone

Product 1

HCID 509159931-[(E)-1-[3-[(7-fluoroquinolin-6-yl)methyl]triazolo[4,5-b]pyrazin-5-yl]ethylideneamino]imidazolidine-2,4-dioneYield 71.5%

Procedure

The title compound (18.0 mg, 66%) was synthesized from 1-[3-(7-fluoro-quinolin-6-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl]-ethanone (20.0 mg, 0.06 mmol) and 1-amino-imidazolidine-2,4-dione (28.2 mg, 0.19 mmol) using the same procedure as described in the synthesis of example 72. 1H-NMR (400 MHz, DMSO-d6) δ ppm 11.45 (bs, 1H), 9.41 (s, 1H), 8.93 (dd, 1H), 8.42 (d, 1H), 8.21 (d, 1H), 7.83 (d, 1H), 7.54 (dd, 1H), 6.26 (s, 2H), 4.56 (s, 2H), 2.45 (s, 3H). LCMS (method B): [MH]+=420, tR=1.95 min.

Workup

  1. customas described in the synthesis of example 72

Sources & evidence

ORD record
ord-85731c5585c14b7f9e962c9c7392199a
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Reaction notes

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