1-Hydroxybenzotriazole → HCID 44612212, compound

HRID 2368398Notes

Reaction equation

HRID 2368398 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:16]=[CH:17][C:18]=1[O:19][CH2:20][CH3:21])[C:7]([NH:9][C:10]([CH3:15])([CH3:14])[C:11]([OH:13])=O)=[O:8])[CH3:2].[CH2:22]([C:29]1[S:33][C:32]([NH2:34])=[N:31][C:30]=1[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>C(#N)C.O>[CH2:22]([C:29]1[S:33][C:32]([NH:34][C:11]([C:10]([NH:9][C:7](=[O:8])[C:6]2[CH:16]=[CH:17][C:18]([O:19][CH2:20][CH3:21])=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=2)([CH3:15])[CH3:14])=[O:13])=[N:31][C:30]=1[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57476890HCID 57476890, compoundHCID 57476891HCID 57476891, compound

Product 1

HCID 44612212HCID 44612212, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

150 mg of 2-(3,4-Diethoxy-benzoylamino)-2-methyl-propionic acid and 130 mg of 5-Benzyl-4-phenyl-thiazol-2-ylamine (WO2006082952) were stirred in 2 ml of acetonitrile at room temperature. 120 mg of EDCl and 100 mg of HOBT were added and the reaction mixture was stirred at 50° C. for 2 days and cooled to room temperature. It was diluted with water and the resulting precipitates were collected by filtration followed by washing with water. The filter cake was then purified by column chromatography (heptane/ethyl acetate=3/1) to provide the title compound. 1H NMR (400 MHz. CD3OD) δ 1.34-1.54 (m, 3H) 1.44 (d, J=5.31 Hz, 3H) 1.65 (s, 7H) 4.14 (qd, J=6.95, 2.53 Hz, 4H) 4.23 (s, 2H) 7.01 (d, J=8.46 Hz, 1H) 7.16-7.26 (m, 3H) 7.26-7.45 (m, 6H) 7.47-7.67 (m, 4H). m/z 545.1 (MH+).

Workup

  1. temperaturecooled to room temperature
  2. customthe resulting precipitates
  3. filtrationwere collected by filtration
  4. washby washing with water
  5. customThe filter cake was then purified by column chromatography (heptane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-acd3131a834d429a8f0c7f640c5dd12a
Source dataset
uspto-grants-2014_04
Patent number
US08703761B2

Reaction notes

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