Ethanolamine → 2-{[2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-ylmethyl]-amino}-ethanol

HRID 1190486Notes

Reaction equation

HRID 1190486 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]=O)[CH:20]=[CH:19][C:16]=4[C:17]=3[N:18]=2)=[N:7][CH:6]=[N:5]1)([CH3:3])[CH3:2].[CH2:25]([CH2:27][NH2:28])[OH:26]>>[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]([CH2:23][NH:28][CH2:27][CH2:25][OH:26])[CH:20]=[CH:19][C:16]=4[C:17]=3[N:18]=2)=[N:7][CH:6]=[N:5]1)([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 700EthanolamineHCID 582036922-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-8-carbaldehyde

Product 1

HCID 582039952-{[2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-ylmethyl]-amino}-ethanol

Procedure

Following the procedure for 212, 2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-8-carbaldehyde and ethanolamine were reacted to give 285 isolated as a pale yellow solid (131 mg, 47%). LCMS: RT=6.85 min, [M+H]+=386. 1H NMR δ (ppm) (CDCl3): 8.31 (1H, d, J=8.11 Hz), 7.89 (1H, s), 7.12 (1H, d, J=8.19 Hz), 7.02 (1H, s), 5.93-5.82 (1H, m), 4.37 (2H, t, J=5.06 Hz), 3.81 (2H, s), 3.66 (2H, t, J=5.12 Hz), 3.38 (2H, t, J=5.06 Hz), 2.81 (2H, t, J=5.11 Hz), 1.60 (6H, d, J=6.63 Hz). 2 Exchangeable protons not seen.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-ddfe6eedee894efaa44a1ff4278a758b
Source dataset
uspto-grants-2014_03
Patent number
US08673952B2

Reaction notes

Loading…