2-Methoxyethylamine → [2-(4-Isopropyl-4H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-ylmethyl]-(2-methoxy-ethyl)-amine

HRID 707875Notes

Reaction equation

HRID 707875 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].[CH3:25][O:26][CH2:27][CH2:28][NH2:29]>>[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:29][CH2:28][CH2:27][O:26][CH3:25])[CH:20]=[CH:19][C:16]=3[C:17]=2[N:18]=1)([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 80182-MethoxyethylamineHCID 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 58204241[2-(4-Isopropyl-4H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-ylmethyl]-(2-methoxy-ethyl)-amineYield 56%

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 2-methoxyethylamine were reacted. After purification by flash chromatography the resulting oil was dissolved in ether and treated with 1M HCl in ether to give a solid that was filtered off and dried to give 120 as a yellow solid (129 mg, 56%). LCMS: RT=6.11 min, [M+H]+=400. 1H NMR δ (ppm) (DMSO-d6): 9.17 (2H, s), 8.93-8.90 (1H, m), 8.29 (1H, d, J=8.13 Hz), 7.28 (1H, dd, J=8.22, 1.81 Hz), 7.24 (1H, d, J=1.76 Hz), 5.47-5.38 (1H, m), 4.33 (2H, t, J=4.98 Hz), 4.10 (2H, t, J=5.38 Hz), 3.56 (2H, t, J=5.15 Hz), 3.43-3.30 (2H, m), 3.25 (3H, s), 3.02 (2H, t, J=5.63 Hz), 1.56-1.49 (6H, m)

Workup

  1. customwere reacted
  2. customAfter purification by flash chromatography the resulting oil
  3. dissolutionwas dissolved in ether
  4. additiontreated with 1M HCl in ether
  5. customto give a solid
  6. filtrationthat was filtered off
  7. customdried

Sources & evidence

ORD record
ord-eda6f3eb538e4fc0b3dacfbbf08bcac3
Source dataset
uspto-grants-2015_11
Patent number
US09175009B2

Reaction notes

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