Diisopropylethylamine → tert-butyl-(2R)-4-((6-bromo-1-oxo-2-(phenylsulfonyl)-1,2-dihydroisoquinolin-4-yl)methyl)-2-(hydroxymethyl)piperazine-1-carboxylate

HRID 906416Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([S:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH:6]=[C:5]2[CH2:22]Br.[CH2:24]([N:26]([C@H:34]([CH2:37][NH:38][CH3:39])[CH2:35][OH:36])[C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])C.C(N(CC)C(C)C)(C)C>C1COCC1.O>[C:29]([O:28][C:27]([N:26]1[CH2:24][CH2:39][N:38]([CH2:22][C:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([Br:1])[CH:3]=3)[C:8](=[O:12])[N:7]([S:13]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)(=[O:14])=[O:15])[CH:6]=2)[CH2:37][C@@H:34]1[CH2:35][OH:36])=[O:33])([CH3:30])([CH3:31])[CH3:32]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 6-bromo-4-(bromomethyl)-2-(phenylsulfonyl)isoquinolin-1(2H)-one (Example 11d, 1.75 g) in THF (20 mL) was treated with (R)-tert-butyl ethyl(1-hydroxy-3-(methylamino)propan-2-yl)carbamate (0.98 g) and N,N-diisopropylethylamine (0.80 mL) under nitrogen. The resulting solution was stirred at 50° C. for 1 h. The reaction mixture was diluted with water (300 mL), and extracted with ethyl acetate (250 mL×2). The combined organics were dried (MgSO4), filtered and evaporated. Triturated with diethyl ether/isohexane (1:1) afforded the subtitle compound (2.30 g) as a solid.

Workup

extractionextracted with ethyl acetate (250 mL×2)
dry with materialThe combined organics were dried (MgSO4)
filtrationfiltered
customevaporated
customTriturated with diethyl ether/isohexane (1:1)

Sources & evidence

ORD record: ord-d3e08493286942f8b6b6ecb8b4cbe243
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012980B2

Reaction notes

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