Ammonia → HCID 67199968, compound

HRID 1711358Notes

Reaction equation

HRID 1711358 reaction equation
[Cl-].[C:2]([NH:5][C:6]1[CH:23]=[CH:22][C:9]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18](N)[CH:19]=3)[NH+:14]=[CH:13][CH:12]=2)=[CH:8][CH:7]=1)(=[O:4])[CH3:3].C=O.[BH3-][C:27]#[N:28].[Na+].[CH3:30]C([O-])=O.[Na+].Cl.N>CO>[CH3:30][N:28]([CH3:27])[C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][CH:12]=[C:11]2[NH:10][C:9]1[CH:22]=[CH:23][C:6]([NH:5][C:2](=[O:4])[CH3:3])=[CH:7][CH:8]=1

Participants

8

Reactant 6

HCID 222AmmoniaHCID 313Hydrochloric Acid2×HCID 712FormaldehydeHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 67202012HCID 67202012, compound

Product 1

HCID 67199968HCID 67199968, compoundYield 101.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of A4 (1.237 g, 3.76 mmol), in MeOH (50 mL) was added 38% aqueous formaldehyde (8.4 mL, 112.8 mmol, 30 eq), NaBH3CN (2.134 g, 30.08 mmol, 8 eq), NaOAc (526 mg, 6.41 mmol) and 2 drops of c. HCl. The reaction mixture was stirred at 20° C. for 2 h, by this time TLC (SiO2/8% MeOH/DCM/aq NH3) and mass spectrum showed completion of the reaction. Then the reaction mixture was acidified with c. HCl, stirred for 1 h. at 20° C. After this time the reaction mixture was carefully neutralize with aqueous NH3. The MeOH was evaporated under reduced pressure and the aqueous residue was the stirred with aqueous NH3. The resulting precipitate was filtered washed with water to give essentially pure A5 (1.22 g, 91%); This was used without further purification; mp, (MeOH)>280° C.; 1H NMR [(CD3)2SO] δ 9.95 (s, 1H, NH), 8.85 (bs, 1H, NH), 8.18 (d, J=5.5 Hz, 1H, ArH), 7.72 (d, J=9.3 Hz, 1H, ArH), 7.65 (d, J=8.8 Hz, 2H, ArH), 7.41 (dd, J=9.3, 2.6 Hz, 1H, ArH), 7.29-7.26 (m, 3H, ArH), 6.67 (d, J=5.5 Hz, 1H, ArH), 3.06 [s, 6H, N(CH3)2], 2.06 (s, 3H, COCH3); APCl+ve 321.

Workup

  1. customcompletion of the reaction
  2. customThe MeOH was evaporated under reduced pressure
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-ad965f96c6234d229649099cb4d9725f
Source dataset
uspto-grants-2010_09
Patent number
US07790746B2

Reaction notes

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