Diisopropylethylamine → HCID 58203818, compound

HRID 1849243Notes

Reaction equation

HRID 1849243 reaction equation
[NH:1]1[CH2:4][CH:3]([C:5]2[CH:26]=[CH:25][C:8]3[C:9]4[N:10]=[C:11]([C:17]5[N:18]([CH:22]([CH3:24])[CH3:23])[N:19]=[CH:20][N:21]=5)[S:12][C:13]=4[CH2:14][CH2:15][O:16][C:7]=3[CH:6]=2)[CH2:2]1.C(N(C(C)C)CC)(C)C.[CH:36]([S:39](Cl)(=[O:41])=[O:40])([CH3:38])[CH3:37]>>[CH:22]([N:18]1[C:17]([C:11]2[S:12][C:13]3[CH2:14][CH2:15][O:16][C:7]4[CH:6]=[C:5]([CH:3]5[CH2:4][N:1]([S:39]([CH:36]([CH3:38])[CH3:37])(=[O:41])=[O:40])[CH2:2]5)[CH:26]=[CH:25][C:8]=4[C:9]=3[N:10]=2)=[N:21][CH:20]=[N:19]1)([CH3:24])[CH3:23]

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 824082-Propanesulfonyl chlorideHCID 582040768-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 58203818HCID 58203818, compound

Procedure

Following the procedure for 395, 8-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 free base 235, diisopropylethylamine and isopropylsulfonyl chloride were reacted. The reaction mixture was loaded directly onto a silica column with no aqueous work-up to give 321 isolated as a solid (57 mg, 25%). LCMS: RT=12.20 min, [M+H]+=474. 1H NMR δ (ppm) (CDCl3): 8.39 (1 H, d, J=8.20 Hz), 7.93 (1 H, s), 7.21 (1 H, dd, J=8.21, 1.89 Hz), 7.06 (1 H, d, J=1.84 Hz), 5.96-5.88 (1 H, m), 4.42 (2 H, t, J=5.00 Hz), 4.29 (2 H, t, J=8.23 Hz), 4.15 (2 H, t, J=7.30 Hz), 3.84-3.78 (1 H, m), 3.43 (2 H, t, J=5.03 Hz), 3.16 (1 H, t, J=6.84 Hz), 1.64 (6 H, d, J=6.62 Hz), 1.40 (6 H, d, J=6.84 Hz)

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-b46f7bc8b72f422e957fd7cf28b7c7e0
Source dataset
uspto-grants-2015_02
Patent number
US08952043B2

Reaction notes

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