Hydrochloric Acid → HCID 86705471, compound

HRID 2279444Notes

Reaction equation

HRID 2279444 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:13][C:14]([N:16]2[CH2:25][CH2:24][C:23]3[CH:22]=[N:21][C:20]([NH:26][CH:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)=[N:19][C:18]=3[CH2:17]2)=[O:15])[C:9]([O:11]C)=[O:10])=[CH:4][C:3]=1[F:33].C1COCC1.[OH-].[Na+].Cl>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:13][C:14]([N:16]2[CH2:25][CH2:24][C:23]3[CH:22]=[N:21][C:20]([NH:26][CH:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)=[N:19][C:18]=3[CH2:17]2)=[O:15])[C:9]([OH:11])=[O:10])=[CH:4][C:3]=1[F:33]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 68295093HCID 68295093, compound

Product 1

HCID 86705471HCID 86705471, compoundYield 45.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 44 (610 mg, 1.28 mmol) and THF (5 mL) was added MeOH (1 mL) followed by the dropwise addition of 1M NaOH (5105 μL, 5.11 mmol). The reaction was stirred for 1 h, cooled to 0° C. and acidified to pH 3 with 1N HCl. The mixture was extracted twice with 10% MeOH in DCM (25 mL). The organic layers were combined and concentrated to afford 270 mg (45.6%) of 2-(4-chloro-3-fluorophenyl)-2-(2-(tetrahydro-2H-pyran-4-ylamino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine-7-carboxamido)acetic acid (46) which was used without further purification.

Workup

  1. extractionThe mixture was extracted twice with 10% MeOH in DCM (25 mL)
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-4f4d17a4c5ff4eb4a8c2e75b4ab048d6
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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