Piperidine → HCID 66977371, compound

HRID 77093Notes

Reaction equation

Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([C:15]([OH:17])=O)[CH2:11][CH2:10]2)=[CH:5][C:4]=1[C:18]1[NH:26][C:21]2[CH:22]=[N:23][CH:24]=[CH:25][C:20]=2[N:19]=1.CN(C(ON1N=N[C:37]2[CH:38]=[CH:39][CH:40]=[N:41][C:36]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.N1CCCCC1>ClCCl>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([C:15]([N:41]3[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]3)=[O:17])[CH2:11][CH2:10]2)=[CH:5][C:4]=1[C:18]1[NH:26][C:21]2[CH:22]=[N:23][CH:24]=[CH:25][C:20]=2[N:19]=1

Participants

Conditions

Temperature: 35 °C

Procedure

Method C—Step f A mixture of 1-[4-Cloro-3-(3H-imidazo[4,5-c]pyridin-2-yl)-phenyl]-piperidine-4-carboxylic acid hydrochloride (0.09 g, 0.25 mmol), HATU (0.10 g, 0.26 mmol), triethylamine (TEA) (0.08 mL, 0.55 mmol), piperidine (0.03 g, 0.31 mmol) and dichloromethane (2 mL) was heated at 35° C. overnight. Reaction was cooled to room temperature, washed with ammonium chloride solution (3 mL) and the crude was purified by SCX (eluent: NH3 2N in MeOH) and flash chromatography (eluent: AcOEt:MeOH, 9:1), to obtain 0.04 g of the title compound (37%).

Workup

customReaction
temperaturewas cooled to room temperature
washwashed with ammonium chloride solution (3 mL)
customthe crude was purified by SCX (eluent: NH3 2N in MeOH) and flash chromatography (eluent: AcOEt:MeOH, 9:1)

Sources & evidence

ORD record: ord-13f7af2c07fa4da18c2e3e27de2246eb
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835648B2

Reaction notes

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