2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-8-{1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-azetidin-3-yl}-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene → 2-{3-[2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-yl]-azetidin-1-yl}-ethanol

HRID 708067Notes

Reaction equation

[CH:1]([N:4]1[C:8]([C:9]2[S:10][C:11]3[CH2:12][CH2:13][O:14][C:15]4[CH:22]=[C:21]([CH:23]5[CH2:26][N:25]([CH2:27][CH2:28][O:29]C6CCCCO6)[CH2:24]5)[CH:20]=[CH:19][C:16]=4[C:17]=3[N:18]=2)=[N:7][CH:6]=[N:5]1)([CH3:3])[CH3:2]>CO>[CH:1]([N:4]1[C:8]([C:9]2[S:10][C:11]3[CH2:12][CH2:13][O:14][C:15]4[CH:22]=[C:21]([CH:23]5[CH2:24][N:25]([CH2:27][CH2:28][OH:29])[CH2:26]5)[CH:20]=[CH:19][C:16]=4[C:17]=3[N:18]=2)=[N:7][CH:6]=[N:5]1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 30 °C

Procedure

Following the procedure for 376, 2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-8-{1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-azetidin-3-yl}-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene was reacted with MeOH as the solvent and the reaction mixture was warmed to 30° C. The crude product was triturated with diethyl ether to give 322 as a yellow solid (92 mg, quant.) LCMS: RT=3.03 min, [M+H]+=412. 1H NMR δ (ppm) (DMSO-d6): 10.65 (1H, s), 8.34-8.25 (1H, m), 8.06 (1H, s), 7.27-7.20 (1H, m), 7.15 (1H, dd, J=14.90, 1.71 Hz), 5.80-5.71 (1H, m), 4.41-4.21 (5H, m), 4.20-4.08 (1H, m), 3.67-3.56 (2H, m), 3.45-3.30 (2H, m), 3.26 (1H, dd, J=10.12, 5.06 Hz), 1.51-1.46 (6H, m). 2 Protons obscured by water peak and 1 exchangeable not observed

Workup

customThe crude product was triturated with diethyl ether

Sources & evidence

ORD record: ord-d903dc69c91f40abbbcc7416b64db9d8
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09175009B2

Reaction notes

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