Dimethylformamide → HCID 18465470, compound

HRID 2230176Notes

Reaction equation

HRID 2230176 reaction equation
Cl.Cl.[NH2:3][CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]([CH:15]2[CH2:20][CH2:19][N:18]([C:21]3([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[CH2:17][CH2:16]2)[C:7]1=[O:34].Br[C:36]1[CH:41]=[CH:40]C=[CH:38][N:37]=1.C([O-])([O-])=O.[K+].[K+].C[N:49](C=O)C>C(Cl)Cl>[C:28]1([C:21]2([N:18]3[CH2:19][CH2:20][CH:15]([N:8]4[C:9]5[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=5[N:6]([CH2:5][CH2:4][NH:3][C:38]5[N:37]=[CH:36][CH:41]=[CH:40][N:49]=5)[C:7]4=[O:34])[CH2:16][CH2:17]3)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 79732-BromopyridineHCID 11430Potassium CarbonateHCID 18465469HCID 18465469, compound

Product 1

HCID 18465470HCID 18465470, compoundYield 8.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(2-aminoethyl)-3-[1-(1-phenylcycloheptyl)-4-piperidinyl]-1,3-dihydro-2H-benzimidazol-2-one dihydrochloride (37.81 mg, 0.0751 mmol, this was prepared according to the procedure of Preparation 18 and Example 64). 2-bromopyridine (14 mg, 0.0901 mol), K2CO3 (36 mg, 0.263 mmol), and DMF (1 ml) was stirred at 60° C. for 4 h. The mixture was diluted with CH2Cl2, washed with water, dried (Na2SO4), filtered, and concentrated. The residue was purified by preparative TLC (acetone/hexane:2/3) to give 3.3 mg (8.6%) of colorless oil.

Workup

  1. customthis was prepared
  2. customaccording to the procedure of Preparation 18 and Example 64)
  3. washwashed with water
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by preparative TLC (acetone/hexane:2/3)

Sources & evidence

ORD record
ord-08c228930a334a77831460065a5841bd
Source dataset
uspto-grants-2002_07
Patent number
US06423725B1

Reaction notes

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