Hydrochloric Acid → HCID 69004781, compound

HRID 1632072Notes

Reaction equation

HRID 1632072 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[C:10]([CH2:16][C:17]3[CH:18]=[CH:19][C:20]([N:23]4[CH2:26][CH2:25][C@H:24]4[C:27]([NH2:29])=[O:28])=[N:21][CH:22]=3)[C:9]=2[F:30])[CH:5]=[CH:6][CH:7]=1.Cl>CCOCC>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[C:10]([CH2:16][C:17]3[CH:18]=[CH:19][C:20]([N:23]4[CH2:26][CH2:25][C@H:24]4[C:27]([NH2:29])=[O:28])=[N:21][CH:22]=3)[C:9]=2[F:30])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58020095HCID 58020095, compound

Product 1

HCID 69004781HCID 69004781, compoundYield 194.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
2.5 °C

Procedure

To a cooled (0-5° C.) and stirred solution of (S)-1-[5-(3′-chloro-2-fluoro-6methoxy-biphenyl-3-ylmethyl)-pyridin-2-yl]-azetidine-2-carboxylic acid amide (P-615, 0.04 g, 0.1 mmol) in ether (2 mL) was added 2M HCl in ether (0.5 ml, 1.0 mmol), and the reaction, stirred for 1 h. The ether layer was removed, again triturated with ether (2.0 mL), concentrated to afford 0.045 g (98%) of P-615-HCl as a white solid. 1H NMR (DMSO-d6, 400 MHz): 7.92 (d, J=2.0 Hz, 1H), 7.78 (d, J=7.6 Hz, 1H), 7.69 (br s, 1H), 7.26-7.48 (m, 6H), 6.95 (d, J=8.8 Hz, 1H), 6.72 (d, J=9.2 Hz, 1H), 4.8-4.9 (m, 1H), 4.0-4.18 (m, 2H), 3.89 (s, 2H), 3.73 (s, 3H), 2.64-2.74 (m 1H), 2.26-2.34 (m, 1H) ppm; MS (APCI+): 426.16 (M+1), LC-MS: 98.8%; HPLC 98.3% pure.

Workup

  1. customthe reaction
  2. customThe ether layer was removed
  3. customagain triturated with ether (2.0 mL)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-db8bc7048e854c7490653b6136559864
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

Loading…