Hydrochloric Acid → HCID 86671947, compound

HRID 709248Notes

Reaction equation

HRID 709248 reaction equation
[CH3:1][C@@:2]([S:34]([CH3:37])(=[O:36])=[O:35])([CH2:13][CH2:14][N:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][C:24]([CH:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[CH:23][CH:22]=2)=[CH:17][C:16]1=[O:33])[C:3]([NH:5][O:6]C1CCCCO1)=[O:4].Cl>CC(O)C>[OH:6][NH:5][C:3](=[O:4])[C@:2]([CH3:1])([S:34]([CH3:37])(=[O:36])=[O:35])[CH2:13][CH2:14][N:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:22]=[CH:23][C:24]([CH:27]3[CH2:28][CH2:29][O:30][CH2:31][CH2:32]3)=[CH:25][CH:26]=2)=[CH:17][C:16]1=[O:33]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86671948(2R)-2-methyl-2-(methylsulfonyl)-4-{2-oxo-4-[4-(tetrahydro-2H-pyran-4-yl)phenyl]pyridin-1(2H)-yl}-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

Product 1

HCID 86671947HCID 86671947, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of (2R)-2-methyl-2-(methylsulfonyl)-4-{2-oxo-4-[4-(tetrahydro-2H-pyran-4-yl)phenyl]pyridin-1(2H)-yl}-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (82 mg, 0.15 mmol) in 2-propanol (1.5 mL) was added 1.0 N hydrochloric acid (0.77 mL). The solution was stirred for 1 h. The reaction was concentrated, the residue was triturated with 2-propanol as a white suspension at 50° C. for 30 minutes. A white solid was collected by filtration (75%). LCMS m/z 449.0 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.57 (s, 3H) 1.65-1.74 (m, 4H) 2.11-2.21 (m, 1H) 2.37-2.47 (m, 1H) 2.83 (tt, J=10.40, 5.42 Hz, 1H) 3.11 (s, 3H) 3.39-3.49 (m, 2H) 3.74 (td, J=12.01, 4.69 Hz, 1H) 3.92-3.99 (m, 2H) 4.11 (td, J=11.91, 5.08 Hz, 1H) 6.65 (dd, J=7.03, 2.15 Hz, 1H) 6.69 (d, J=2.15 Hz, 1H) 7.37 (m, 2H) 7.67 (m, 2H) 7.74 (d, J=7.23 Hz, 1H) 9.27 (br. s., 1H) 11.19 (s, 1H).

Workup

  1. concentrationThe reaction was concentrated
  2. customthe residue was triturated with 2-propanol as a white suspension at 50° C. for 30 minutes
  3. filtrationA white solid was collected by filtration (75%)

Sources & evidence

ORD record
ord-21edcea95a8d436cb29d21c673b87e7d
Source dataset
uspto-grants-2015_11
Patent number
US09180123B2

Reaction notes

Loading…