Triethylamine → HCID 136105554, compound

HRID 1690002Notes

Reaction equation

HRID 1690002 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19]C)[N:3]=1.COC1C=CC=CC=1C1N=[C:37]([NH:39][CH2:40][C:41]2[O:42][C:43]([CH3:46])=[N:44][N:45]=2)C2C(=CC(C)=CC=2)N=1.C(O)(=O)C(O)=O.CC1OC(CN)=NN=1.C(N(CC)CC)C>CN(C=O)C>[CH3:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([N:39]([CH3:37])[CH2:40][C:41]3[O:42][C:43]([CH3:46])=[N:44][N:45]=3)=[N:3][C:4]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[OH:19])=[N:5]2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 53445292HCID 53445292, compoundHCID 86595329HCID 86595329, compound

Product 1

HCID 136105554HCID 136105554, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

[2-(2-Methoxy-phenyl)-7-methyl-quinazolin-4-yl]-(5-methyl-[1,3,4]oxadiazol-2-ylmethyl)-amine 4-Chloro-2-(2-methoxy-phenyl)-7-methyl-quinazoline (400 mg, 1.48 mmol) was dissolved in 10 ml dry DMF followed by the addition of C-(5-Methyl-[1,3,4]oxadiazol-2-yl)-methylamine oxalate (234 mg, 1.48 mmol) then triethylamine (413 μl, 2.96 mmol). After 6 hours the reaction was complete, partitioned between EtOAc and water. The organic phase was separated, dried over MgSO4, filtered and concentrated to an oil. Purified by flash chromatography 60% EtOAc/40% hexanes to afford the desired product a white solid. Recovered 290 mg 56% yield. LC/MS (10-99%) M/Z 348.4, retention time 2.17 minutes.

Workup

  1. custompartitioned between EtOAc and water
  2. customThe organic phase was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to an oil
  6. customPurified by flash chromatography 60% EtOAc/40% hexanes

Sources & evidence

ORD record
ord-13060565f6b6458a91ee8bbb1c150acf
Source dataset
uspto-grants-2012_04
Patent number
US08153642B2

Reaction notes

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