Water → 1-[6-(3-{4-Amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl]-1,2,4-oxadiazol-5-yl)pyridin-3-yl}ethyl 2,2,2-trichloroethanecarboximidate

HRID 341499Notes

Reaction equation

HRID 341499 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]([CH3:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:5]=[C:4]([C:16]2[N:20]=[C:19]([C:21]3[N:26]=[CH:25][C:24]([CH:27]([OH:29])[CH3:28])=[CH:23][CH:22]=3)[O:18][N:17]=2)[N:3]=1.[Cl:30][C:31]([Cl:35])([Cl:34])[C:32]#N.[N:36]1(C2CCCCCCCCCC2)CCCN=CCCCC[CH2:37]1.O>C(Cl)Cl>[Cl:30][C:31]([Cl:35])([Cl:34])[CH2:32][C:37](=[NH:36])[O:29][CH:27]([C:24]1[CH:25]=[N:26][C:21]([C:19]2[O:18][N:17]=[C:16]([C:4]3[N:3]=[C:2]([NH2:1])[N:7]=[C:6]([N:8]([CH3:15])[C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=4)[N:5]=3)[N:20]=2)=[CH:22][CH:23]=1)[CH3:28]

Participants

6

Reactant 4

HCID 962WaterHCID 11011TrichloroacetonitrileHCID 668031951-[6-(3-{4-Amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl]-1,2,4-oxadiazol-5-yl)pyridin-3-yl}ethan-1-ol2×HCID 1296629601,8-Diazabicycloundec-7ene

Product 1

HCID 668027621-[6-(3-{4-Amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl]-1,2,4-oxadiazol-5-yl)pyridin-3-yl}ethyl 2,2,2-trichloroethanecarboximidateYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-[6-(3-{4-Amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl}-1,2,4-oxadiazol-5-yl)pyridin-3-yl]ethan-1-ol (Intermediate 140, 0.400 g, 1.02 mmol) was suspended in DCM. Trichloroacetonitrile (0.123 mL, 1.22 mmol) and 1,8-diazabicycloundec-7-ene (few drops) were added and the mixture was stirred at room temperature for 19 h. DCM (30 mL) and water (30 mL) were added, the organic layer was separated and washed with brine (30 mL), before being dried over sodium sulfate and concentrated under vacuum to afford the title compound as a golden-brown solid (0.497 g, 91%), which was used in the next step without further purification. Method C HPLC-MS: MH+ requires m/z=534 Found: m/z=534, Rt=1.55 min (57%).

Workup

  1. customthe organic layer was separated
  2. washwashed with brine (30 mL)
  3. dry with materialbefore being dried over sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-d7c52dbed6844ba1b98c1c7681c50f04
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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