Hydrochloric Acid → HCID 11522376, compound

HRID 2246898Notes

Reaction equation

HRID 2246898 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:18]=[CH:17][C:12]2[N:13]=[CH:14][N:15]([CH3:16])[C:11]=2[C:10]=1[C:19]#[N:20].Cl.[OH-].[NH4+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:18]=[CH:17][C:12]2[N:13]=[CH:14][N:15]([CH3:16])[C:11]=2[C:10]=1[CH2:19][NH2:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 11659451HCID 11659451, compound

Product 1

HCID 11522376HCID 11522376, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Borane-THF complex in THF (1 M, 2 mL, 2 mmol) was added to a solution of Example 6B in dry THF (6 mL) at r.t. The reaction stirred at reflux for 1 h, and was then cooled to 0° C. Concentrated HCl (0.8 mL) was added slowly, and the reaction was stirred at 60° C. for 1 h. The solution was cooled to 0° C., made basic with ammonium hydroxide, and extracted (3×) with EtOAc. Organics were dried (MgSO4) and concentrated in vacuo. Purification by Prep-HPLC gave 88 mg (51%) white solid as the HCl salt. 1H NMR (400 MHz, MeOD-d4): δ 9.59 (s, 1H), 8.04 (d, 1H, J=8.4 Hz), 7.71 (d, 1H, J=2.0 Hz), 7.50-7.59 (m, 3H), 4.51 (qAB, 2H, J=142.4, 15.2 Hz), 4.45 (s, 3H). MS (ES) [m+H] calc'd for C15H13N3Cl2, 306, 308; found 306, 308.

Workup

  1. temperatureat reflux for 1 h
  2. stirringthe reaction was stirred at 60° C. for 1 h
  3. temperatureThe solution was cooled to 0° C.
  4. extractionextracted (3×) with EtOAc
  5. dry with materialOrganics were dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customPurification by Prep-HPLC

Sources & evidence

ORD record
ord-887ad93f68a149d89e23c2f048546d93
Source dataset
uspto-grants-2010_03
Patent number
US07687638B2

Reaction notes

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