Hydrochloric Acid → 3-(1-Benzylpiperidin-4-yl)-3H-imidazo[4,5-b]pyridine

HRID 1068169Notes

Reaction equation

[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[C:20]([NH2:21])=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:22](OC)(OC)OC.Cl>>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:15]3=[N:16][CH:17]=[CH:18][CH:19]=[C:20]3[N:21]=[CH:22]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 9005Trimethyl orthoformate

HCID 21192982N2-(1-benzylpiperidin-4-yl)pyridine-2,3-diamine

Product 1

HCID 209553953-(1-Benzylpiperidin-4-yl)-3H-imidazo[4,5-b]pyridine

Procedure

The title compound was prepared from 153 mg of 2-N-(1-benzyl-piperidin-4-yl)-pyridine-2,3-diamine (from Step B), 6 mL of trimethyl orthoformate, and) 0.2 mL of concentrated HCl, using a procedure analogous to that described in Example 95, Step B to provide 139 mg of the title compound as a yellow solid.

Sources & evidence

ORD record: ord-37c7e1b97e2b44cfb7df55872c5c4b9a
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06248755B1

Reaction notes

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