Hydrochloric Acid → 6,7-Dihydro-4-hydroxy-7-isobutyl-6-oxo-n-(3-(piperidin-1-yl)propyl)thieno[2,3-b]pyridine-5-carboxamide hydrochloride salt

HRID 1724662Notes

Reaction equation

HRID 1724662 reaction equation
[OH:1][C:2]1[C:3]2[CH:27]=[CH:26][S:25][C:4]=2[N:5]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:6](=[O:20])[C:7]=1[C:8]([NH:10][CH2:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:9].[ClH:28].C(OCC)C>ClCCl>[ClH:28].[OH:1][C:2]1[C:3]2[CH:27]=[CH:26][S:25][C:4]=2[N:5]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:6](=[O:20])[C:7]=1[C:8]([NH:10][CH2:11][CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1)=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 546839606,7-dihydro-4-hydroxy-7-isobutyl-6-oxo-N-(3-(piperidin-1-yl)propyl)thieno[2,3-b]pyridine-5-carboxamide

Product 1

HCID 547492076,7-Dihydro-4-hydroxy-7-isobutyl-6-oxo-n-(3-(piperidin-1-yl)propyl)thieno[2,3-b]pyridine-5-carboxamide hydrochloride saltYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6,7-dihydro-4-hydroxy-7-isobutyl-6-oxo-N-(3-(piperidin-1-yl)propyl)thieno[2,3-b]pyridine-5-carboxamide (0.11 g, 0.28 mmol) in dichloromethane (0.2 mL) was added hydrogen chloride (0.6 mL, 0.6 mmol, 1.0 M solution in diethyl ether). The reaction mixture became cloudy immediately. Additional amount of diethyl ether was added to cause more solid precipitation. These precipitates were collected by vacuum filtration, washed with ether and dried to give the title compound as an off-white solid (0.11 g, 92% yield). 1H NMR (400 MHz, CDCl3): δ 7.39 (d, 1 H), 7.11 (d, 1 H), 3.96 (d, 2 H), 3.60-2.25 (m, 8 H), 2.19-1.79 (m, 8 H), 0.99 (d, 6 H); MS: m/e 392 (M+H+).

Workup

  1. customsolid precipitation
  2. filtrationThese precipitates were collected by vacuum filtration
  3. washwashed with ether
  4. customdried

Sources & evidence

ORD record
ord-789918cf69514fd8b670ccec3062fdb9
Source dataset
uspto-grants-2009_02
Patent number
US07488736B2

Reaction notes

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