Hydrochloric Acid → HCID 178434483, compound

HRID 1034950Notes

Reaction equation

HRID 1034950 reaction equation
N1C=CC=CC=1.Cl.[CH3:8][C:9]1[C:21]2[C:20]3[CH:19](N4CCN(C)CC4)[CH2:18][CH2:17][CH2:16][C:15]=3[C:14](=[O:29])[NH:13][C:12]=2[N:11](C)[N:10]=1.[OH-].[Na+]>ClCCl.O>[CH3:8][C:9]1[C:21]2[C:20]3[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=3[C:14](=[O:29])[NH:13][C:12]=2[NH:11][N:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 14798Sodium HydroxideHCID 136341275HCID 136341275, compound

Product 1

HCID 178434483HCID 178434483, compoundYield 85.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
230 °C

Procedure

A mixture of 8.5 g of pyridine and 10 mL of concentrated hydrochloric acid was heated to 230° C., added to EXAMPLE 1 (217 mg, 1.0 mmol) and the mixture heated at 230° C. for 2 hours. After cooling, water was added and the suspension neutralized with 10% sodium hydroxide. Dichloromethane (50 mL) was added, the mixture was filtered and the solid collected, washed with dichloromethane and water and dried. Purification by HPLC (Zorbax, C-18, 250×2.54 column, Mobile phase A: 0.1% trifluoroacetic acid in water; B: 0.1% trifluoroacetic acid in acetonitrile; 0-100% gradient) provided 173 mg (73%) of the title compound as the trifluoroacetate salt. 1H NMR (DMSO-d6) 1.63-1.73 (m, 4H), 2.29-2.34 (m, 2H), 2.46 (s, 3H), 2.75-2.80 (m, 2H), 11.28 (br s, 1H).

Workup

  1. temperaturethe mixture heated at 230° C. for 2 hours
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered
  4. customthe solid collected
  5. washwashed with dichloromethane and water
  6. customdried
  7. customPurification by HPLC (Zorbax, C-18, 250×2.54 column, Mobile phase A: 0.1% trifluoroacetic acid in water; B: 0.1% trifluoroacetic acid in acetonitrile; 0-100% gradient)

Sources & evidence

ORD record
ord-c8f0de76e96b4c60a2d197f81987cd91
Source dataset
uspto-grants-2013_10
Patent number
US08546368B2

Reaction notes

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