Diisopropylethylamine → (S)-1-(4-bromobenzyl)-N-(1-(3-isopropylphenyl)ethyl)-1H-benzo[d]imidazole-5-carboxamide

HRID 626405Notes

Reaction equation

HRID 626405 reaction equation
[Br:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[CH:13][C:14]([C:16]([OH:18])=O)=[CH:15][C:10]=3[N:9]=[CH:8]2)=[CH:4][CH:3]=1.[CH:21]([C:24]1[CH:25]=[C:26]([C@@H:30]([NH2:32])[CH3:31])[CH:27]=[CH:28][CH:29]=1)([CH3:23])[CH3:22].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[CH:13][C:14]([C:16]([NH:32][C@H:30]([C:26]4[CH:27]=[CH:28][CH:29]=[C:24]([CH:21]([CH3:23])[CH3:22])[CH:25]=4)[CH3:31])=[O:18])=[CH:15][C:10]=3[N:9]=[CH:8]2)=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 285381601-(4-bromobenzyl)-1H-benzo[d]imidazole-5-carboxylic acidHCID 86674570(S)-1-(3-isopropylphenyl)ethanamine

Product 1

HCID 118072722(S)-1-(4-bromobenzyl)-N-(1-(3-isopropylphenyl)ethyl)-1H-benzo[d]imidazole-5-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The mixture of 1-(4-bromobenzyl)-1H-benzo[d]imidazole-5-carboxylic acid (521 mg, 1.57 mmol), (S)-1-(3-isopropylphenyl)ethanamine (314 mg, 1.88 mmol), HATU (1.19 g, 1.88 mmol) and DIPEA (607 mg, 4.71 mmol) in DMF (15 mL) was stirred at RT overnight. Then the mixture was poured into 20 mL of water, then extracted with EtOAc (10 mL×3). The combined organic layers was washed with water (10 mL) and brine (10 mL) and dried with Na2SO4. After filtration, the filtrate was concentrated under the reduced pressure. The residue was purified with Combiflash (DCM/EtOAc=4/1, silica gel) to give the title compound.

Workup

  1. extractionextracted with EtOAc (10 mL×3)
  2. washThe combined organic layers was washed with water (10 mL) and brine (10 mL)
  3. dry with materialdried with Na2SO4
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated under the reduced pressure
  6. customThe residue was purified with Combiflash (DCM/EtOAc=4/1, silica gel)

Sources & evidence

ORD record
ord-6648f7bb1619455b90180fa7d29009ba
Source dataset
uspto-grants-2016_04
Patent number
US09309227B2

Reaction notes

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