Diisopropylethylamine → (1R)-1-(2,2-Dimethyl4H-1,3-benzodioxin-6-yl)-2-({6-[4-(1,1-dioxido-3,4-dihydro-2H-thiochromen-7-yl)butoxy]hexyl}amino)ethanol

HRID 1593035Notes

Reaction equation

[NH2:1][CH2:2][C@@H:3]([C:5]1[CH:16]=[CH:15][C:8]2[O:9][C:10]([CH3:14])([CH3:13])[O:11][CH2:12][C:7]=2[CH:6]=1)[OH:4].C(N(C(C)C)CC)(C)C.Br[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38]1[CH:47]=[C:46]2[C:41]([CH2:42][CH2:43][CH2:44][S:45]2(=[O:49])=[O:48])=[CH:40][CH:39]=1>O1CCCC1.CN(C)C=O>[CH3:14][C:10]1([CH3:13])[O:9][C:8]2[CH:15]=[CH:16][C:5]([C@@H:3]([OH:4])[CH2:2][NH:1][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38]3[CH:47]=[C:46]4[C:41]([CH2:42][CH2:43][CH2:44][S:45]4(=[O:49])=[O:48])=[CH:40][CH:39]=3)=[CH:6][C:7]=2[CH2:12][O:11]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of (1R)-2-amino-1-(2,2-dimethyl4H-1,3-benzodioxin-6-yl)ethanol (128 mg) in dry tetrahydrofuran (6 ml) and dimethylformamide (2 ml) was added diisopropylethylamine (0.066 ml) and 7-{4[(6-bromohexyl)oxy]butyl}thiochromane 1,1-dioxide (120 mg). The reaction mixture was heated at 50° C. for 17 h. The mixture was then concentrated in vacuo and the residue was purified by chromatography on a Biotage cartridge (8 g) eluting with dichloromethane-ethanol-aqueous ammonia solution (100:8:1) to give the title compound (134 mg). LCMS RT=2.74 min

Workup

concentrationThe mixture was then concentrated in vacuo
customthe residue was purified by chromatography on a Biotage cartridge (8 g)
washeluting with dichloromethane-ethanol-aqueous ammonia solution (100:8:1)

Sources & evidence

ORD record: ord-9957eb4aede749348d029cf24282625d
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07294650B2

Reaction notes

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