3-Hydroxypiperidine, (R)- → N8-[4-(tert-Butyl)-1,3-thiazol-2-yl]-2-[(3R)-3-hydroxyhexahydro-1-pyridinyl]-4-oxo-4H-pyrido[1,2-a]pyrimidine-8-carboxamide

HRID 1828465Notes

Reaction equation

HRID 1828465 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([NH:10][C:11]([C:13]2[CH:35]=[CH:34][N:16]3[C:17](=[O:33])[C:18](/C=C/C(O)=O)=[C:19]([N:21]4[CH2:26][CH2:25][CH2:24][C@@H:23]([OH:27])[CH2:22]4)[N:20]=[C:15]3[CH:14]=2)=[O:12])[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C(C1N=C(NC(C2C=CN3C(=O)CC(=O)N=C3C=2)=O)SC=1)(C)(C)C.O[C@@H]1CCCNC1>>[C:1]([C:5]1[N:6]=[C:7]([NH:10][C:11]([C:13]2[CH:35]=[CH:34][N:16]3[C:17](=[O:33])[CH:18]=[C:19]([N:21]4[CH2:26][CH2:25][CH2:24][C@@H:23]([OH:27])[CH2:22]4)[N:20]=[C:15]3[CH:14]=2)=[O:12])[S:8][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 27593343-Hydroxypiperidine, (R)-HCID 22063754N8-[4-(tert-butyl)-1,3-thiazol-2-yl]-2,4-dioxo-3,4-dihydro-2H-pyrido[1,2-a]pyrimidine-8-carboxamideHCID 23581329(E)-3-{8-({[4-(tert-Butyl)-1,3-thiazol-2-yl]amino}carbonyl)-2-[(3R)-3-hydroxyhexahydro-1-pyridinyl]-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-propenoic acid

Product 1

HCID 23581334N8-[4-(tert-Butyl)-1,3-thiazol-2-yl]-2-[(3R)-3-hydroxyhexahydro-1-pyridinyl]-4-oxo-4H-pyrido[1,2-a]pyrimidine-8-carboxamideYield 65%

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 (300 mg, 0.871 mmol) and (R)-(+)-3-hydroxypiperidine (530 mg, 5.226 mmol) to obtain 241.8 mg (65%) of the title compound.

Sources & evidence

ORD record
ord-f04338fcfd6e4984883e10300f4d10a3
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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