Piperidine → 4-[1-Ethyl-7-((R)-2-piperazin-1-ylmethyl-cyclopentylmethyl)-1H-imidazo[4,5-c]pyridin-2-yl]-furazan-3-ylamine

HRID 1394212Notes

Reaction equation

HRID 1394212 reaction equation
[NH2:1][C:2]1[C:3]([C:7]2[N:8]([CH2:24][CH3:25])[C:9]3[C:14]([CH2:15]NC4CCNCC4)=[CH:13][N:12]=[CH:11][C:10]=3[N:23]=2)=[N:4][O:5][N:6]=1.[CH:26]([N:29](C(C)C)[CH2:30][CH3:31])(C)[CH3:27].[C:35](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH:49]1[CH2:54][CH2:53][CH2:52][CH2:51][CH2:50]1>ClCCCl>[CH2:24]([N:8]1[C:9]2[C:14]([CH2:15][C@H:35]3[CH2:50][CH2:51][CH2:52][CH:53]3[CH2:54][N:49]3[CH2:31][CH2:30][NH:29][CH2:26][CH2:27]3)=[CH:13][N:12]=[CH:11][C:10]=2[N:23]=[C:7]1[C:3]1[C:2]([NH2:1])=[N:6][O:5][N:4]=1)[CH3:25]

Participants

6

Reactant 4

HCID 8082PiperidineHCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 11393719SB-747651A

Product 1

HCID 691581304-[1-Ethyl-7-((R)-2-piperazin-1-ylmethyl-cyclopentylmethyl)-1H-imidazo[4,5-c]pyridin-2-yl]-furazan-3-ylamineYield 19%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

The product of example 191 step 1 (100 mg, 0.387 mmol) was dissolved in 1,2-dichloroethane (2.5 ml) and added to a stirred solution of the product of Step 1 (480 mg, 0.774 mmol) and diisopropyl ethylamine (100 mg, 0.774 mmol) in 1,2-dichloroethane (2.5 ml). After stirring for 5 minutes the reaction was treated with sodium triacetoxyborohydride (164 mg, 0.774 mmol) and the reaction was stirred for 16 hours at room temperature. The reaction was then treated with piperidine (5 ml) and stirred for 5 hours at room temperature. The solvent was then evaporated in vacuo and the residue diluted with dichloromethane, washed with saturated sodium bicarbonate solution, water, brine, dried over anhydrous sodium sulfate and evaporated iv vacuo. The residue was purified by automated reverse phase chromatography (Biotage flex, acetonitrile/water eluant) to afford the title compound (30 mg, 19%); MS (ES+), m/e 412 [M+H]+.

Workup

  1. stirringthe reaction was stirred for 16 hours at room temperature
  2. stirringstirred for 5 hours at room temperature
  3. customThe solvent was then evaporated in vacuo
  4. additionthe residue diluted with dichloromethane
  5. washwashed with saturated sodium bicarbonate solution, water, brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated iv vacuo
  8. customThe residue was purified by automated reverse phase chromatography (Biotage flex, acetonitrile/water eluant)

Sources & evidence

ORD record
ord-c6b07219d7b24296a7d9c07cc51ca021
Source dataset
uspto-grants-2008_03
Patent number
US07348339B2

Reaction notes

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