[3-(2-Chloro-oxazol-5-yl)-phenyl]-(4-methyl-pyrimidin-2-yl)-amine → 1-(2-Methoxy-ethyl)-4-{5-[3-(4-methyl-pyrimidin-2-ylamino)-phenyl]-oxazol-2-yl}-piperazin-2-one

HRID 1854609Notes

Reaction equation

HRID 1854609 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[CH:35]=[C:36]([NH:40][C:41]3[N:46]=[C:45]([CH3:47])[CH:44]=[CH:43][N:42]=3)[CH:37]=[CH:38][CH:39]=2)=[CH:32][N:33]=1.FC(F)(F)C(O)=O.[CH3:55][O:56][CH2:57][CH2:58][N:59]1[CH2:64][CH2:63][NH:62][CH2:61][C:60]1=[O:65]>CC(O)C>[CH3:55][O:56][CH2:57][CH2:58][N:59]1[CH2:64][CH2:63][N:62]([C:29]2[O:30][C:31]([C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([NH:40][C:41]4[N:46]=[C:45]([CH3:47])[CH:44]=[CH:43][N:42]=4)[CH:35]=3)=[CH:32][N:33]=2)[CH2:61][C:60]1=[O:65]

Participants

5

Reactant 3

HCID 67323670[3-(2-Chloro-oxazol-5-yl)-phenyl]-(4-methyl-pyrimidin-2-yl)-amineHCID 673458655-[6-(4-methylpyridin-2-ylamino)pyridin-2-yl]-N-(pyridin-4-ylmethyl)oxazol-2-amineHCID 673748961-(2-Methoxy-ethyl)-2-oxopiperazine trifluoroacetic acid salt

Product 1

HCID 673255951-(2-Methoxy-ethyl)-4-{5-[3-(4-methyl-pyrimidin-2-ylamino)-phenyl]-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 [3-(2-chloro-oxazol-5-yl)-phenyl]-(4-methyl-pyrimidin-2-yl)-amine and 1-(2-methoxy-ethyl)-2-oxopiperazine trifluoroacetic acid salt in iPrOH. 1H NMR (400 MHz, DMSO-d6) δ 9.56 (s, 1H), 8.35 (d, J=5.0 Hz, 1H), 8.10 (s, 1H), 7.64 (d, J=8.0 Hz, 1H), 7.31-7.20 (m, 2H), 7.15 (d, J=7.6 Hz, 1H), 6.76 (d, J=5.0 Hz, 1H), 4.10 (s, 2H), 3.79-3.72 (m, 2H), 3.58-3.46 (m, 6H), 3.25 (dd, J=2.7, 2.2 Hz, 3H), 2.38 (s, 3H). (ESI+) m/z 409 (M+H)+. Retention time=2.94 mins (method 1).

Sources & evidence

ORD record
ord-80fda699512a498692edc80c85befa41
Source dataset
uspto-grants-2015_02
Patent number
US08962665B2

Reaction notes

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