1-Aminoimidazolidin-2-one → HCID 71699930, compound

HRID 456174

Reaction equation

HRID 456174 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][CH2:29][NH:28][C:27]1=[O:31]>>[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][CH2:29][NH:28][C:27]3=[O:31])/[CH3:23])[N:20]=2)[N:15]=[N:14]1

Participants

3

Reactant 2

HCID 1816971-Aminoimidazolidin-2-oneHCID 581905781-[3-(7-Fluoro-quinolin-6-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl]-ethanone

Product 1

HCID 71699930HCID 71699930, compoundYield 74%

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-imidazolidin-2-one (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 9.42 (s, 1H), 8.93 (dd, 1H), 8.41 (d, 1H), 8.20 (d, 1H), 7.83 (d, 1H), 7.54 (dd, 1H), 7.38 (s, 1H), 6.25 (s, 2H), 3.86 (t, 2H), 3.42 (t, 2H), 2.38 (s, 3H). LCMS (method A): [MH]+=401, tR=2.01 min.

Workup

  1. customas described in the synthesis of example 72

Sources & evidence

ORD record
ord-df8007f44176414997637c634e03c98f
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Linked notes

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