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

HRID 1849064Notes

Reaction equation

HRID 1849064 reaction equation
[CH:1]([N:4]1[CH:8]=[N:7][N:6]=[C:5]1[C:9]1[S:10][C:11]2[CH2:12][CH2:13][O:14][C:15]3[CH:22]=[C:21]([CH:23]=O)[CH:20]=[CH:19][C:16]=3[C:17]=2[N:18]=1)([CH3:3])[CH3:2].[CH2:25]([CH2:27][NH2:28])[OH:26]>>[CH:1]([N:4]1[CH:8]=[N:7][N:6]=[C:5]1[C:9]1[S:10][C:11]2[CH2:12][CH2:13][O:14][C:15]3[CH:22]=[C:21]([CH2:23][NH:28][CH2:27][CH2:25][OH:26])[CH:20]=[CH:19][C:16]=3[C:17]=2[N:18]=1)([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 700EthanolamineHCID 582037272-(4-Isopropyl-4H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-8-carbaldehyde

Product 1

HCID 582037412-{[2-(4-Isopropyl-4H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-ylmethyl]-amino}-ethanolYield 27%

Procedure

Following the procedure for 119, 2-(4-isopropyl-4H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-8-carbaldehyde and ethanolamine were reacted. After aqueous work-up the resulting gum was triturated with DCM/ether/pentane to give a solid that was filtered off and dried to give 131 as an off-white solid (55 mg, 27%). LCMS: RT=5.54 min, [M+H]+=386. 1H NMR δ (ppm) (CDCl3): 8.37 (1 H, s), 8.30 (1 H, d, J=8.11 Hz), 7.13 (1 H, dd, J=8.15, 1.72 Hz), 7.05 (1 H, d, J=1.68 Hz), 5.70-5.63 (1 H, m), 4.41 (2 H, t, J=5.06 Hz), 3.84 (2 H, s), 3.68 (2 H, t, J=5.17 Hz), 3.42 (2 H, t, J=5.07 Hz), 2.85 (2 H, t, J=5.16 Hz), 1.65 (6 H, d, J=6.74 Hz). 2 Exchangeable protons not seen

Workup

  1. customwere reacted
  2. customAfter aqueous work-up the resulting gum was triturated with DCM/ether/pentane
  3. customto give a solid
  4. filtrationthat was filtered off
  5. customdried

Sources & evidence

ORD record
ord-95ce37e7f75e4c36813e71eaa7c23d24
Source dataset
uspto-grants-2015_02
Patent number
US08952043B2

Reaction notes

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