Hydrochloric Acid → HCID 68735414, compound

HRID 1890416Notes

Reaction equation

HRID 1890416 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([NH:8][CH:9]2[C:15]3=[N:16][C:17]([C:21]4[CH:26]=[CH:25][N:24]=[CH:23][N:22]=4)=[CH:18][C:19](=[O:20])[N:14]3[CH2:13][CH2:12][NH:11][CH2:10]2)=[O:7])=[C:4]([O:29][CH3:30])[CH:3]=1.C=O.[C:33](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl>CO.C(O)(=O)C>[ClH:1].[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([NH:8][CH:9]2[C:15]3=[N:16][C:17]([C:21]4[CH:26]=[CH:25][N:24]=[CH:23][N:22]=4)=[CH:18][C:19](=[O:20])[N:14]3[CH2:13][CH2:12][N:11]([CH3:33])[CH2:10]2)=[O:7])=[C:4]([O:29][CH3:30])[CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 712Formaldehyde2×HCID 5049666Sodium triacetoxyborohydride2×HCID 44195246HCID 44195246, compound

Product 1

HCID 68735414HCID 68735414, compoundYield 162.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of 0.040 g (0.09 mmol) of (+/−)-4-chloro-2-methoxy-N-(4-oxo-2-pyrimidin-4-yl-4,5,6,7,8,9-hexahydro-1,4a,7-triaza-benzocyclohepten-9-yl)-benzamide in 1.9 ml of methanol was added 0.003 g (0.04 mmol) of paraformaldehyde, 0.022 g (0.10 mmol) of sodium triacetoxyborohydride and 40 μL (0.20 mmol) of hydrochloric acid (5-6N in isopropanol). The reaction mixture was stirred at room temperature for 12 hours. To the resulting mixture was added 0.006 g (0.07 mmol) of paraformaldehyde 0.042 g (0.20 mmol) of sodium triacetoxyborohydride and pH was adjusted to 6 with glacial acetic acid. The resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated; the residue was dissolved in dichloromethane, washed with a saturated aqueous solution of sodium carbonate, saturated aqueous solution of sodium chloride, dried over sodium sulfate and evaporated. The free base was transformed into its hydrochloride salt to give 0.035 g of pure product.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 2 hours
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe residue was dissolved in dichloromethane
  4. washwashed with a saturated aqueous solution of sodium carbonate, saturated aqueous solution of sodium chloride
  5. dry with materialdried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-20ce186fab3b4fbc828a99540dde00a3
Source dataset
uspto-grants-2013_08
Patent number
US08507476B2

Reaction notes

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