Phenylacetic Acid → HCID 66743320, compound

HRID 2363978Notes

Reaction equation

HRID 2363978 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[S:15][C:14]3[C:13](=[O:16])[NH:12][C:11]4([CH2:21][CH2:20][NH:19][CH2:18][CH2:17]4)[NH:10][C:9]=3[CH:8]=2)=[CH:3][CH:2]=1.[C:22]1([CH2:28][C:29](O)=[O:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)C(C)C)(C)C.Cl.C(N=C=NCCCN(C)C)C.OC1C2N=NNC=2C=CC=1.C([O-])(O)=O.[Na+]>CN(C=O)C>[C:22]1([CH2:28][C:29]([N:19]2[CH2:20][CH2:21][C:11]3([NH:10][C:9]4[CH:8]=[C:7]([C:4]5[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=5)[S:15][C:14]=4[C:13](=[O:16])[NH:12]3)[CH2:17][CH2:18]2)=[O:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

8

Reactant 6

HCID 999Phenylacetic AcidHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66742948HCID 66742948, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 66743320HCID 66743320, compoundYield 21.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 6′-(pyridin-4-yl)-1′H-spiro [piperidine-4,2′-thieno[3,2-d]pyrimidin]-4′(3′H)-one (0.050 g, 0.17 mmol) in DMF (5 mL) were added phenylacetic acid (0.030 g, 0.22 mmol), N,N-diisopropylethylamine (0.12 mL, 0.68 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.050 g, 0.26 mmol) and hydroxybenzotriazole (0.035 g, 0.26 mmol). The mixture was allowed to stir overnight. Then, the reaction was poured into saturated NaHCO3 (75 mL) and the mixture was extracted with 3:1 tetrahydrofuran/ethyl acetate (3×75 mL). The combined organic layers were concentrated and the residue was diluted with water (5 mL) and sonicated for 1 min. Then, the solids were collected by filtration to give the title compound (0.0151 g, 21%) as a yellow solid:

Workup

  1. extractionthe mixture was extracted with 3:1 tetrahydrofuran/ethyl acetate (3×75 mL)
  2. concentrationThe combined organic layers were concentrated
  3. additionthe residue was diluted with water (5 mL)
  4. customsonicated for 1 min
  5. filtrationThen, the solids were collected by filtration

Sources & evidence

ORD record
ord-03f6285f317e45fdb700fdbd797afcf1
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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