(E)-3-{8-[2-(4-Ethyl-2-thienyl)ethyl]-2-morpholino-4-oxo-4H-pyrido[1,2-a]-pyrimidin-3-yl}-2-propenoic acid → tert-Butyl (E)-3-[8-{[(4-cyclobutyl-1,3-thiazol-2-yl)amino]carbonyl}-2-(3-formyloxy-piperidino)-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl]-2-propenoate

HRID 1828458Notes

Reaction equation

HRID 1828458 reaction equation
C(C1C=C(CCC2C=CN3C(=O)C(/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27])=C(N4CCOCC4)N=C3C=2)SC=1)C.[CH:32]([O:34][CH:35]1[CH2:40][CH2:39][CH2:38][N:37]([C:41]2[N:42]=[C:43]3[CH:53]=[C:52]([C:54]([NH:56][C:57]4[S:58][CH:59]=[C:60]([CH:62]5[CH2:65][CH2:64][CH2:63]5)[N:61]=4)=[O:55])[CH:51]=[CH:50][N:44]3[C:45](=[O:49])[C:46]=2C=O)[CH2:36]1)=[O:33]>>[CH:62]1([C:60]2[N:61]=[C:57]([NH:56][C:54]([C:52]3[CH:51]=[CH:50][N:44]4[C:45](=[O:49])[C:46](/[CH:24]=[CH:25]/[C:26]([O:28][C:52]([CH3:54])([CH3:53])[CH3:51])=[O:27])=[C:41]([N:37]5[CH2:38][CH2:39][CH2:40][CH:35]([O:34][CH:32]=[O:33])[CH2:36]5)[N:42]=[C:43]4[CH:53]=3)=[O:55])[S:58][CH:59]=2)[CH2:63][CH2:64][CH2:65]1

Participants

3

Reactant 2

HCID 22063594(E)-3-{8-[2-(4-Ethyl-2-thienyl)ethyl]-2-morpholino-4-oxo-4H-pyrido[1,2-a]-pyrimidin-3-yl}-2-propenoic acidHCID 220636821-(8-{[(4-cyclobutyl-1,3-thiazol-2-yl)amino]carbonyl}-3-formyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-2-yl)-3-piperidyl formate

Product 1

HCID 86588104tert-Butyl (E)-3-[8-{[(4-cyclobutyl-1,3-thiazol-2-yl)amino]carbonyl}-2-(3-formyloxy-piperidino)-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl]-2-propenoate

Procedure

Reactions were performed in the same manner as in Example 1, (J) by using 1-(8-{[(4-cyclobutyl-1,3-thiazol-2-yl)amino]carbonyl}-3-formyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-2-yl)-3-piperidyl formate (36 mg, 0.075 mmol), and the resulting reaction solution was purified by thin layer silica gel chromatography (chloroform:methanol=30:1) to obtain 35 mg of the title compound as orange crystals in a mixture with triphenylphosphine oxide.

Workup

  1. customthe resulting reaction solution
  2. customwas purified by thin layer silica gel chromatography (chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-1209d68fcd2c4388a868bff337f67897
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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