Diisopropylethylamine → 8-[1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethyl)-azetidin-3-yl]-2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene

HRID 1190287Notes

Reaction equation

HRID 1190287 reaction equation
C([N:4]1[CH2:7][CH:6]([C:8]2[CH:29]=[CH:28][C:11]3[C:12]4[N:13]=[C:14]([C:20]5[N:21]([CH:25]([CH3:27])[CH3:26])[N:22]=[CH:23][N:24]=5)[S:15][C:16]=4[CH2:17][CH2:18][O:19][C:10]=3[CH:9]=2)[CH2:5]1)(C)C.[CH3:30][C:31]1([CH3:38])[O:35][C@@H:34]([CH:36]=O)[CH2:33][O:32]1.C(N(C(C)C)CC)(C)C>>[CH3:30][C:31]1([CH3:38])[O:35][C@@H:34]([CH2:36][N:4]2[CH2:5][CH:6]([C:8]3[CH:29]=[CH:28][C:11]4[C:12]5[N:13]=[C:14]([C:20]6[N:21]([CH:25]([CH3:27])[CH3:26])[N:22]=[CH:23][N:24]=6)[S:15][C:16]=5[CH2:17][CH2:18][O:19][C:10]=4[CH:9]=3)[CH2:7]2)[CH2:33][O:32]1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 259712(R)-2,2-dimethyl-1,3-dioxolane-4-carbaldehydeHCID 582042038-(1-isopropyl-azetidin-3-yl)-2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene

Product 1

HCID 582041408-[1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-ylmethyl)-azetidin-3-yl]-2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene

Procedure

The title compound was prepared by a similar procedure to 8-(1-isopropyl-azetidin-3-yl)-2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene using (R)-(+)-2,2-dimethyl-1,3-dioxolane-4-carboxaldehyde instead of acetone and adding 1.0 eq. diisopropylethylamine to the reaction mixture. The product was isolated as a colourless oil (127 mg, 32%). LCMS: RT=3.37 min, [M+H]+=482

Sources & evidence

ORD record
ord-ebed21b43d1a4accb534a215614915f3
Source dataset
uspto-grants-2014_03
Patent number
US08673952B2

Reaction notes

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