Acetaldehyde → HCID 136090378, compound

HRID 131502Notes

Reaction equation

HRID 131502 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C@@H:5]1[NH:10][CH2:9][CH2:8][N:7]([C:11]2[C:20]3[N:19]=[C:18]([C:21]([F:24])([F:23])[F:22])[S:17][C:16]=3[NH:15][C:14]3[CH:25]=[CH:26][CH:27]=[CH:28][C:13]=3[N:12]=2)[CH2:6]1.[CH:29](=O)[CH3:30]>>[CH2:29]([N:10]1[CH2:9][CH2:8][N:7]([C:11]2[C:20]3[N:19]=[C:18]([C:21]([F:23])([F:24])[F:22])[S:17][C:16]=3[NH:15][C:14]3[CH:25]=[CH:26][CH:27]=[CH:28][C:13]=3[N:12]=2)[CH2:6][C@@H:5]1[CH2:4][CH2:3][O:2][CH3:1])[CH3:30]

Participants

3

Reactant 2

HCID 177AcetaldehydeHCID 135457486(S)-10-[3-(2-Methoxy-ethyl)-piperazin-1-yl]-2-trifluoromethyl-4H-3-thia-1,4,9-triaza-benzo[f]azulene

Product 1

HCID 136090378HCID 136090378, compound

Procedure

Using the method of Example 346 using (5)-10-[3-(2-methoxy-ethyl)-piperazin-1-yl]-2-trifluoromethyl-4H-3-thia-1,4,9-triaza-benzo[f]azulene and acetaldehyde at ambient temperature, and purification by flash chromatography, eluting with a gradient of a 5% solution of 2M ammonia in methanol, in dichloromethane, (0-50% over 25 minutes, 50% for 10 minutes, 50-100% over 23 minutes, 100% for 5 minutes) gives the title compound: mass spectrum (APCI, m/e): 440 (M+1); NMR (1H, 300 MHz, DMSO-d6), δ (ppm): δ 8.47 (s, 1H), 6.96-6.81 (m, 3H), 6.71 (m, 1H), 3.50 (br. m, 3H), 3.35-3.21 (m, 2H), 3.21-3.07 (m, 4H), 2.76-2.51 (m, 3H), 2.37 (m, 2H), 1.67 (m, 2H), 0.96 (t, 3H, J=6.9 Hz).

Workup

  1. customat ambient temperature
  2. custompurification by flash chromatography
  3. washeluting with a gradient of a 5% solution of 2M ammonia in methanol, in dichloromethane

Sources & evidence

ORD record
ord-09f59616d81c4d1e8bb8ee11eda3ff41
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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