Methanol → HCID 68752443, compound

HRID 1912927Notes

Reaction equation

HRID 1912927 reaction equation
[CH:1]1([CH2:6][CH2:7][C:8](Cl)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:11][C:12]1[C:20]([C:21]([O:23][CH3:24])=[O:22])=[C:15]2[N:16]=[CH:17][CH:18]=[CH:19][N:14]2[N:13]=1.CO>C(Cl)Cl.N1C=CC=CC=1>[CH:1]1([CH2:6][CH2:7][C:8]([NH:11][C:12]2[C:20]([C:21]([O:23][CH3:24])=[O:22])=[C:15]3[N:16]=[CH:17][CH:18]=[CH:19][N:14]3[N:13]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 887MethanolHCID 660393-Cyclopentylpropionyl chlorideHCID 68751071HCID 68751071, compound

Product 1

HCID 68752443HCID 68752443, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-cyclopentylpropionyl chloride (0.58 mL, 3.8 mmol) in CH2Cl2 (0.5 mL) was added to a suspension of the product from Example 125A (300 mg, 1.56 mmol) in pyridine (5 mL) at room temperature. After 4 hours, methanol (10 mL) was added to quench the excess acyl chloride, and the mixture was stirred for 15 minutes, and then concentrated under vacuum. The residue was crystallized from 86% methanol-water (24 mL) to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.01-1.22 (m, 2H) 1.39-1.69 (m, 6H) 1.68-1.88 (m, 3H) 2.46-2.54 (m, 2H) 3.81 (s, 3H) 7.25 (dd, J=6.9, 4.2 Hz, 1H) 8.75 (dd, J=4.4, 1.6 Hz, 1H) 9.18 (dd, J=6.9, 1.8 Hz, 1H) 10.04 (s, 1H); MS (ESI) m/z 317 (M+H)+; Anal. Calculated for C16H20N4O3: C, 60.75; H, 6.37; N, 17.71. Found: C, 60.71; H, 5.85; N, 17.48.

Workup

  1. customto quench the excess acyl chloride
  2. concentrationconcentrated under vacuum
  3. customThe residue was crystallized from 86% methanol-water (24 mL)

Sources & evidence

ORD record
ord-d7b51bdfdd7d4296867b6ca78b54f0f0
Source dataset
uspto-grants-2013_12
Patent number
US08609669B2

Reaction notes

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