Piperazin-2-one → 4-{5-[6-(5-Methyl-thiazol-2-ylamino)-pyridin-2-yl]-oxazol-2-yl}-piperazin-2-one

HRID 1854607Notes

Reaction equation

HRID 1854607 reaction equation
CC1C=CN=C(NC2N=C(C3OC(NCC4C=CN=CC=4)=NC=3)C=CC=2)C=1.Cl[C:29]1[O:30][C:31]([C:34]2[N:39]=[C:38]([NH:40][C:41]3[S:42][C:43]([CH3:46])=[CH:44][N:45]=3)[CH:37]=[CH:36][CH:35]=2)=[CH:32][N:33]=1.[O:47]=[C:48]1[CH2:53][NH:52][CH2:51][CH2:50][NH:49]1>CC(O)C>[CH3:46][C:43]1[S:42][C:41]([NH:40][C:38]2[N:39]=[C:34]([C:31]3[O:30][C:29]([N:52]4[CH2:51][CH2:50][NH:49][C:48](=[O:47])[CH2:53]4)=[N:33][CH:32]=3)[CH:35]=[CH:36][CH:37]=2)=[N:45][CH:44]=1

Participants

5

Reactant 3

HCID 231360Piperazin-2-oneHCID 673458655-[6-(4-methylpyridin-2-ylamino)pyridin-2-yl]-N-(pyridin-4-ylmethyl)oxazol-2-amineHCID 86676500[6-(2-Chloro-oxazol-5-yl)-pyridin-2-yl]-(5-methyl-thiazol-2-yl)-amine

Product 1

HCID 866764994-{5-[6-(5-Methyl-thiazol-2-ylamino)-pyridin-2-yl]-oxazol-2-yl}-piperazin-2-one

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Prepared as for 5-[6-(4-methylpyridin-2-ylamino)pyridin-2-yl]-N-(pyridin-4-ylmethyl)oxazol-2-amine above from [6-(2-Chloro-oxazol-5-yl)-pyridin-2-yl]-(5-methyl-thiazol-2-yl)-amine and 2-oxopiperazine in iPrOH. 1H NMR (400 MHz, DMSO-d6) δ 11.08 (s, 1H), 8.14 (s, 1H), 7.68 (t, J=7.9 Hz, 1H), 7.59 (s, 1H), 7.16-6.97 (m, 2H), 6.83 (d, J=8.2 Hz, 1H), 4.11 (s, 2H), 3.86-3.63 (m, 2H), 3.43-3.32 (m, 2H), 2.37 (s, 3H). (ESI+) m/z 357 (M+H)+. Retention time=1.91 mins (method 1).

Sources & evidence

ORD record
ord-afd8822563504ef7a8340853764b4bf3
Source dataset
uspto-grants-2015_02
Patent number
US08962665B2

Reaction notes

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