(3S)-Piperidin-3-ol--hydrogen chloride (1/1) → N8-[4-(tert-Butyl)-1,3-thiazol-2-yl]-2-[(3S)-3-hydroxyhexahydro-1-pyridinyl]-4-oxo-4H-pyrido[1,2-a]pyrimidine-8-carboxamide

HRID 1828468Notes

Reaction equation

HRID 1828468 reaction equation
NC([O:4][C@H:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]2[N:12]=[C:13]3[CH:26]=[C:25]([C:27]([NH:29][C:30]4[S:31][CH:32]=[C:33]([C:35]([CH3:38])([CH3:37])[CH3:36])[N:34]=4)=[O:28])[CH:24]=[CH:23][N:14]3[C:15](=[O:22])[C:16]=2/C=C/C(O)=O)[CH2:6]1)=O.C(C1N=C(NC(C2C=CN3C(=O)CC(=O)N=C3C=2)=O)SC=1)(C)(C)C.Cl.O[C@H]1CCCNC1>>[C:35]([C:33]1[N:34]=[C:30]([NH:29][C:27]([C:25]2[CH:24]=[CH:23][N:14]3[C:15](=[O:22])[CH:16]=[C:11]([N:7]4[CH2:8][CH2:9][CH2:10][C@H:5]([OH:4])[CH2:6]4)[N:12]=[C:13]3[CH:26]=2)=[O:28])[S:31][CH:32]=1)([CH3:38])([CH3:36])[CH3:37]

Participants

4

Reactant 3

HCID 16211918(3S)-Piperidin-3-ol--hydrogen chloride (1/1)HCID 22063754N8-[4-(tert-butyl)-1,3-thiazol-2-yl]-2,4-dioxo-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine-8-carboxamideHCID 23581314(E)-3-[2-{(3S)-3-[(Aminocarbonyl)oxy]hexahydro-1-pyridinyl}-8-({[4-(tert-butyl)-1,3-thiazol-2-yl]amino}carbonyl)-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl]-2-propenoic acid

Product 1

HCID 23581335N8-[4-(tert-Butyl)-1,3-thiazol-2-yl]-2-[(3S)-3-hydroxyhexahydro-1-pyridinyl]-4-oxo-4H-pyrido[1,2-a]pyrimidine-8-carboxamideYield 62%

Procedure

Reactions were performed in the same manner as in Example 8, (E) by using N8-[4-(tert-butyl)-1,3-thiazol-2-yl]-2,4-dioxo-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine-8-carboxamide (600 mg, 1.74 mmol) and (S)-(−)-3-hydroxypiperidine hydrochloride (360 mg, 2.61 mmol) to obtain 463 mg (62%) of the title compound.

Sources & evidence

ORD record
ord-83f2ba85a8784b598f86f5dafb43708c
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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