Hydrochloric Acid → HCID 58415292, compound

HRID 2075243Notes

Reaction equation

HRID 2075243 reaction equation
[Li+].[OH-].[CH2:3]([C:10]1[CH:11]=[C:12]2[O:19][C:18]([C:20]3[CH:25]=[CH:24][C:23]([CH2:26][N:27]4[CH2:30][CH:29]([C:31]([O:33]C)=[O:32])[CH2:28]4)=[CH:22][C:21]=3[F:35])=[CH:17][C:13]2=[N:14][C:15]=1[Cl:16])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.P([O-])([O-])([O-])=O.Cl>O.C1COCC1>[CH2:3]([C:10]1[CH:11]=[C:12]2[O:19][C:18]([C:20]3[CH:25]=[CH:24][C:23]([CH2:26][N:27]4[CH2:30][CH:29]([C:31]([OH:33])=[O:32])[CH2:28]4)=[CH:22][C:21]=3[F:35])=[CH:17][C:13]2=[N:14][C:15]=1[Cl:16])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1061PhosphateHCID 3939Lithium HydroxideHCID 58415364HCID 58415364, compound

Product 1

HCID 58415292HCID 58415292, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of LiOH (0.022 g, 0.90 mmol) in water (3.0 mL) was added methyl 1-((4-(6-benzyl-5-chlorofuro[3,2-b]pyridin-2-yl)-3-fluorophenyl)methyl)azetidine-3-carboxylate (0.084 g, 0.18 mmol) in THF (2.0 mL). The solution was stirred for 30 min and then the solvent was removed under reduced pressure to afford a white suspension. To the mixture was added 0.5M phosphate buffer, pH 6.0 (3 mL), and then 1 N HCl was added until the pH was 6.0 as indicated by pH paper. The resulting suspension was filtered, and the off white solid was collected and dried under vacuum at 50° C. 1H NMR (400 MHz, DMSO-d6 with 1 drop of TFA-d) 8 ppm 8.04-8.21 (2H, m), 7.44-7.70 (3H, m), 7.18-7.40 (5H, m), 4.45-4.60 (2H, m), 4.13-4.40 (6H, m), 3.60-3.76 (1H, m); MS (ESI) m/z: Calculated: 450.1; Observed: 451.1 (M++1).

Workup

  1. customthe solvent was removed under reduced pressure
  2. customto afford a white suspension
  3. filtrationThe resulting suspension was filtered
  4. customthe off white solid was collected
  5. customdried under vacuum at 50° C

Sources & evidence

ORD record
ord-60f071d68d6447558a8aa14dd20d378c
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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