Hydrochloric Acid → HCID 67199988, compound

HRID 547540Notes

Reaction equation

HRID 547540 reaction equation
[CH3:1][N:2]([CH3:24])[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[NH:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20]C(=O)C)=[CH:16][CH:15]=1.[ClH:25]>O1CCOCC1.CO.CCOC(C)=O>[Cl-:25].[NH2:20][C:17]1[CH:18]=[CH:19][C:14]([NH:13][C:6]2[C:5]3[C:10](=[CH:11][CH:12]=[C:3]([N:2]([CH3:1])[CH3:24])[CH:4]=3)[NH+:9]=[CH:8][CH:7]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67199968HCID 67199968, compound

Product 1

HCID 67199988HCID 67199988, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 21584119Ethylacetate methanolSolvent

Conditions

Temperature
20 °C

Procedure

To a suspension of A5 in 1,4-dioxane (20 mL) was added 1.5 M aq HCl (5 mL) and the reaction mixture was refluxed for 2 h. The reaction mixture was then diluted with MeOH/EtOAc, brought to boil and allowed to cool to 20° C. The resulting precipitate was filtered, washed with EtOAc and dried to give essentially pure A6 as a pale yellow solid (1.20 g, 100%); mp (MeOH/EtOAc) 152-155; 1H NMR [(CD3)2SO] 14.35 (br, 1 H, N+H), 10.50 (br, 2 H, NH2), 8.27 (d, J=6.6 Hz, 1 H, ArH), 7.92 (d, J=9.4 Hz, 1 H, ArH), 7.65 (dd, J=9.5, 2.6 Hz, 1 H, ArH), 7.57 (d, J=2.4 Hz, 1 H, ArH), 7.54 (d, J=8.5 Hz, 2 H, ArH), 7.41 (d, J=8.1 Hz, 2H, ArH), 6.68 (d, J=6.7 Hz, 1 H, ArH), 3.12 (s, 6 H, [N(CH3)2]; APCI+ve 279.

Workup

  1. temperaturethe reaction mixture was refluxed for 2 h
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with EtOAc
  4. customdried

Sources & evidence

ORD record
ord-1ca0a6caa84f49019f90ecb67751288e
Source dataset
uspto-grants-2011_05
Patent number
US07939546B2

Reaction notes

Loading…