Hydrochloric Acid → HCID 86703174, compound

HRID 2204374Notes

Reaction equation

HRID 2204374 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:44])[CH2:7][C:8]1[CH:13]=[C:12]([C:14]2[N:18]([CH:19]([CH3:21])[CH3:20])[C:17]3[CH:22]([C:34]4[CH:39]=[CH:38][C:37]([C:40]#[N:41])=[CH:36][CH:35]=4)[N:23]([C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:27]=4[F:33])[C:24](=[O:25])[C:16]=3[CH:15]=2)[C:11]([O:42][CH3:43])=[CH:10][N:9]=1)C.Cl>CO.C1COCC1.O>[Cl:32][C:28]1[C:27]([F:33])=[C:26]([N:23]2[C:24](=[O:25])[C:16]3[CH:15]=[C:14]([C:12]4[C:11]([O:42][CH3:43])=[CH:10][N:9]=[C:8]([CH2:7][C:6]([OH:44])=[O:5])[CH:13]=4)[N:18]([CH:19]([CH3:21])[CH3:20])[C:17]=3[CH:22]2[C:34]2[CH:39]=[CH:38][C:37]([C:40]#[N:41])=[CH:36][CH:35]=2)[CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86703175HCID 86703175, compound

Product 1

HCID 86703174HCID 86703174, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2N Aqueous NaOH (0.906 mmol) was added to a solution of {4-[5-(3-chloro-2-fluoro-phenyl)-6-(4-cyano-phenyl)-1-isopropyl-4-oxo-1,4,5,6-tetrahydro-pyrrolo[3,4-b]pyrrol-2-yl]-5-methoxy-pyridin-2-yl}-acetic acid ethyl ester (Step 84.1) (0.227 mmol) in MeOH (0.4 mL) and THF (0.4 mL) at 0° C. After stirring for 30 min, the reaction mixture was diluted with H2O, acidified to pH 3-4 with 1N aqueous HCl and then extracted with EtOAc (2×). The combined organic layers were dried (MgSO4), filtered and concentrated. The title compound was obtained as a white solid. tR: 4.51 min (HPLC 4); ESI-MS: tR=0.99 min, [M+H]+ 559/561 (LC-MS 1).

Workup

  1. extractionextracted with EtOAc (2×)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0b848e2e8d2644009b1c39da902c608d
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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