Diisopropylethylamine → HCID 178478310, compound

HRID 983433Notes

Reaction equation

HRID 983433 reaction equation
[Cl:1][C:2]1[N:6]([C:7]2[N:12]=[C:11](Cl)[N:10]=[CH:9][N:8]=2)[C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]=2[N:3]=1.CCN(C(C)C)C(C)C.[NH:27]1[C:31]([CH2:32][C:33]2[CH:34]=[C:35]([NH2:39])[CH:36]=[CH:37][CH:38]=2)=[N:30][N:29]=[N:28]1>CN(C=O)C>[Cl:1][C:2]1[N:6]([C:7]2[N:8]=[CH:9][N:10]=[C:11]([NH:39][C:35]3[CH:36]=[CH:37][CH:38]=[C:33]([CH2:32][C:31]4[NH:30][N:29]=[N:28][N:27]=4)[CH:34]=3)[N:12]=2)[C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 22560124HCID 22560124, compoundHCID 178507551HCID 178507551, compound

Product 1

HCID 178478310HCID 178478310, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
67.5 °C

Procedure

To crude 2-chloro-1-(4-chloro-[1,3,5]triazin-2-yl)-1H-benzimidazole was added DIEA (381 μl, 2.184 mmol) and then a solution of DMF (1 ml) and 3-(1H-tetrazol-5-ylmethyl)phenylamine (382.7 mg, 2.1845 mmol). The reaction was heated at 60-75° C. for 18 h. The reaction was cooled to RT and concentrated to a small volume. The crude was eluted on a silica gel column with a MeOH/CH2Cl2 elution gradient, giving [4-(2-chloro-benzimidazol-1-yl)-[1,3,5]triazin-2-yl]-[3-(1H-tetrazol-5-ylmethyl)-phenyl]amine.

Workup

  1. temperatureThe reaction was cooled to RT
  2. concentrationconcentrated to a small volume
  3. washThe crude was eluted on a silica gel column with a MeOH/CH2Cl2 elution gradient

Sources & evidence

ORD record
ord-cc14a790a7274d50900af71e5b33fd75
Source dataset
uspto-grants-2005_03
Patent number
US06864255B2

Reaction notes

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