tert-butyl (3S)-3-aminopiperidine-1-carboxylate → HCID 57526820, compound

HRID 1452619Notes

Reaction equation

[Si:1]([O:8][CH2:9][CH2:10][C:11]1[C:12](Cl)=[N:13][C:14]2[N:15]([N:36]=[CH:37][CH:38]=2)[C:16]=1[N:17]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][O:34][CH3:35])=[CH:27][CH:26]=1)[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH2:40][C@H:41]1[CH2:46][CH2:45][CH2:44][N:43]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[CH2:42]1>C(#N)C>[C:20]([O:19][C:18]([N:17]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][O:34][CH3:35])=[CH:27][CH:26]=1)[C:16]1[N:15]2[N:36]=[CH:37][CH:38]=[C:14]2[N:13]=[C:12]([NH:40][C@H:41]2[CH2:46][CH2:45][CH2:44][N:43]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[CH2:42]2)[C:11]=1[CH2:10][CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[O:24])([CH3:23])([CH3:22])[CH3:21]

Participants

Conditions

Temperature: 85 °C

Procedure

To an acetonitrile (5 mL) solution containing tert-butyl {6-[2-(tert-butyldimethylsilanyloxy)ethyl]-5-chloropyrazolo[1,5-a]pyrimidin-7-yl}[4-(2-methoxyethoxy)phenyl]carbamate (570 mg, 1.20 mmol), (S)-3-amino-1-tert-butoxycarbonylpiperidine (1.51 g) was added, and this mixture was stirred at 85° C. for 48 hr. The reaction solution was concentrated, and the residue was purified with column chromatography (35% ethyl acetate-hexane) to obtain the title compound (204 mg).

Workup

additionwas added
concentrationThe reaction solution was concentrated
customthe residue was purified with column chromatography (35% ethyl acetate-hexane)

Sources & evidence

ORD record: ord-ec18eaecbbeb46c3ba2a6c5675c32eb0
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07473694B2

Reaction notes

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