Piperidine → Methyl 3-benzyloxy-5-methyl-4-oxo-7-(piperidin-1-ylcarbonyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylate

HRID 1453841Notes

Reaction equation

HRID 1453841 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:23]([O:25][CH3:26])=[O:24])=[N:11][N:12]2[CH:17]([C:18](O)=[O:19])[CH2:16][N:15]([CH3:21])[C:14](=[O:22])[C:13]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>>[CH2:1]([O:8][C:9]1[C:10]([C:23]([O:25][CH3:26])=[O:24])=[N:11][N:12]2[CH:17]([C:18]([N:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)=[O:19])[CH2:16][N:15]([CH3:21])[C:14](=[O:22])[C:13]=12)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 8082PiperidineHCID 68954276HCID 68954276, compound

Product 1

HCID 68953428Methyl 3-benzyloxy-5-methyl-4-oxo-7-(piperidin-1-ylcarbonyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylate

Procedure

The title compound was prepared from 3-benzyloxy-2-methoxycarbonyl-5-methyl-4-oxo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-7-carboxylic acid using a procedure similar to that described in Example 2, Step 5 except that piperidine was used in place of 4-fluorobenzylamine, and the reaction time totaled 18 hours. 1H NMR (400 MHz, d6-DMSO) δ 7.50-7.48 (m, 2H), 7.40-7.31 (m, 3H), 5.88 (d, J=2.4 Hz, 1H), 5.19 (dd, J=11.2, 25.6 Hz, 2H), 4.14 (dd, J=5.2, 13.6 Hz, 1H), 3.78 (s, 3H), 3.68-3.52 (m, 4H), 3.34-3.33 (m, 1H), 2.98 (s, 3H), 1.62 (br s, 4H), 1.47 (br s, 2H); ES MS (M+H)=427.

Sources & evidence

ORD record
ord-3ba6c4b65ef34aafa3d746279fbbf04d
Source dataset
uspto-grants-2009_01
Patent number
US07476666B2

Reaction notes

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