tert-butyl N-(azetidin-3-ylmethyl)carbamate → HCID 66954282, compound

HRID 1511778Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][N:5]=[C:6]2[C:11]=1[N:10]=[C:9]([O:12][CH3:13])[CH:8]=[CH:7]2.[C:14]([O:18][C:19](=[O:26])[NH:20][CH2:21][CH:22]1[CH2:25][NH:24][CH2:23]1)([CH3:17])([CH3:16])[CH3:15]>C(O)CCCC>[C:14]([O:18][C:19](=[O:26])[NH:20][CH2:21][CH:22]1[CH2:23][N:24]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[N:10]=3)[N:5]=[CH:4][CH:3]=2)[CH2:25]1)([CH3:17])([CH3:15])[CH3:16]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 8-bromo-2-methoxy-[1,5]naphthyridine (495 mg, 2.07 mmol, prepared as in WO 2006/032466) and tert-butyl-[(azetidin-3-yl)methyl]carbamate (405 mg, 1.05 eq) in pentanol (2 mL) was heated at 80° C. overnight. The majority of the solvent was removed in vacuo at elevated temperature (50-60° C.). The residue was triturated with ether to form the desired intermediate as beige solid (300 mg, 42%).

Workup

customThe majority of the solvent was removed in vacuo at elevated temperature (50-60° C.)
customThe residue was triturated with ether

Sources & evidence

ORD record: ord-b985621ec81548c98001139cf49c96e0
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217029B2

Reaction notes

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