Diisopropylethylamine → Benzimidazole

HRID 1788555Notes

Reaction equation

HRID 1788555 reaction equation
ClC1C=CC(C2C([C:12]3C=C[C:19]4[C:14](=[CH:15][CH:16]=[C:17](C(O)=O)[CH:18]=4)[N:13]=3)=CC(OC)=CC=2)=CC=1.C[N:30](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[N:30]1[C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[NH:13][CH:12]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 860273132-(4'-Chloro-4-methoxy-biphen-2-yl)-quinoline-6-carboxylic acid

Product 1

HCID 5798Benzimidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Compound 525c (0.38 g, 0.97 mmol) was reacted with HBTU (0.444 g, 1.2 mmol) in anhydrous DMF (5 mL) in the presence of DIEA (0.41 mL, 2.35 mmol) for 30 min. The mixture was then transferred to a suspension of amine-resin in DMF (5 mL). The reaction mixture was shaken at room temperature overnight. The solution was drained and the resin was washed with DMF (5 mL×5), MeOH (5 mL×5), and CH2Cl2 (5 mL×5). The resin was dried under high vacuum.

Workup

  1. washthe resin was washed with DMF (5 mL×5), MeOH (5 mL×5), and CH2Cl2 (5 mL×5)
  2. customThe resin was dried under high vacuum

Sources & evidence

ORD record
ord-2267f3d53bda4933bade31f83b91eb23
Source dataset
uspto-grants-2009_03
Patent number
US07511145B2

Reaction notes

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