Phenylacetic Acid → HCID 68752965, compound

HRID 1912941Notes

Reaction equation

HRID 1912941 reaction equation
[C:1]([C:5]1[C:6]([NH2:14])=[N:7][N:8]2[CH:13]=[CH:12][CH:11]=[N:10][C:9]=12)([CH3:4])([CH3:3])[CH3:2].[C:15]1([CH2:21][C:22](O)=[O:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl.CN(C)CCCN=C=NCC>N1C=CC=CC=1.CN(C=O)C>[C:1]([C:5]1[C:6]([NH:14][C:22](=[O:23])[CH2:21][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:7][N:8]2[CH:13]=[CH:12][CH:11]=[N:10][C:9]=12)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 999Phenylacetic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 687554713-Tert-butylpyrazolo[1,5-a]pyrimidin-2-amine

Product 1

HCID 68752965HCID 68752965, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture from Example 105B (103.8 mg, 0.55 mmol), phenylacetic acid (138.6 mg, 1.02 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide HCL (206.7 mg, 1.08 mmol) in pyridine (1.5 mL) and DMF (1.5 mL) was stirred at ambient temperature for 5 hours. The mixture was concentrated. Purification by reverse phase HPLC afforded 123.7 mg (74%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.39 (s, 9H), 3.63 (s, 2H), 6.99 (dd, J=7.1, 4.1 Hz, 1H), 7.23-7.34 (m, 5H), 8.48 (dd, J=4.1, 1.7 Hz, 1H), 8.91 (dd, J=7.1, 1.7 Hz, 1H), 9.93 (s, 1H); MS (DCI) m/z 309 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. customPurification by reverse phase HPLC

Sources & evidence

ORD record
ord-da132568226b48c3bcae8783becabb38
Source dataset
uspto-grants-2013_12
Patent number
US08609669B2

Reaction notes

Loading…