Diisopropylethylamine → HCID 66954803, compound

HRID 1511785Notes

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]([NH:21][C@H:22]1[CH2:26][CH2:25][NH:24][CH2:23]1)=[O:20])([CH3:17])([CH3:16])[CH3:15].CCN(C(C)C)C(C)C>C(O)CCCC>[C:14]([O:18][C:19](=[O:20])[NH:21][C@H:22]1[CH2:26][CH2:25][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)[CH2:23]1)([CH3:17])([CH3:15])[CH3:16]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 8-bromo-2-methoxy-[1,5]naphthyridine (1.50 g, 6.27 mmol, prepared as in WO 2006/032466) and (S)-(−)-3-(tert-butoxycarbonylamino)pyrrolidine (1.17 g, 6.27 mmol) in pentanol (5 mL) and DIPEA (1.24 mL, 1.2 eq) was heated at 80° C. over night. The majority of the solvent was removed in vacuo at elevated temperature (50-60° C.). The residue was triturated with ether to remove residual amine. The mother liquor was concentrated and the residue was chromatographed over SiO2 (DCM-MeOH—NH4OH 1000:50:4) to afford the desired intermediate as a beige foam (1.86 g, 86%).

Workup

customThe majority of the solvent was removed in vacuo at elevated temperature (50-60° C.)
customThe residue was triturated with ether
customto remove residual amine
concentrationThe mother liquor was concentrated
customthe residue was chromatographed over SiO2 (DCM-MeOH—NH4OH 1000:50:4)

Sources & evidence

ORD record: ord-07487abbe0374947be2c1de14c9d2fa5
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217029B2

Reaction notes

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