Formaldehyde → HCID 131730999, compound

HRID 2035531Notes

Reaction equation

HRID 2035531 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[N:19]=[CH:18][C:17]([CH2:20][C:21]([NH2:23])=[O:22])=[C:16]([NH:24][CH2:25][CH:26]4[CH2:30][CH2:29][CH2:28][NH:27]4)[CH:15]=3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.C=O.[C:33](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl.O.C(O)(=O)C>[CH3:33][N:27]1[CH2:28][CH2:29][CH2:30][CH:26]1[CH2:25][NH:24][C:16]1[CH:15]=[C:14]([NH:13][C:10]2[CH:11]=[CH:12][C:7]([N:4]3[CH2:3][CH2:2][O:1][CH2:6][CH2:5]3)=[CH:8][CH:9]=2)[N:19]=[CH:18][C:17]=1[CH2:20][C:21]([NH2:23])=[O:22]

Participants

8

Reactant 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 131730997HCID 131730997, compound2×

Product 1

HCID 131730999HCID 131730999, compoundYield 70.2%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

37.9 mg of 6-[(4-morpholinophenyl)amino]-4-[(pyrrolidin-2-ylmethyl)amino]pyridine-3-carboxyamide (the compound of Example 358) was dissolved in 2 mL of methylene chloride, to which, under ice cooling, 19.4 mg of 37% formaldehyde in water, 40.5 mg of sodium triacetoxyborohydride and acetic acid were sequentially added, and stirred at room temperature for 2 hours. To the reaction mixture, saturated sodium bicarbonate in water was added, extracted with chloroform:methanol=10:1, the extract washed with saturated saline, and dried on anhydrous sodium sulfate. The solvent was evaporated, and the residue was recrystallized from chloroform-ether to obtain 27.5 mg (70%) of the title compound as a light yellow crystalline powder.

Workup

  1. extractionextracted with chloroform
  2. washmethanol=10:1, the extract washed with saturated saline
  3. dry with materialdried on anhydrous sodium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was recrystallized from chloroform-ether

Sources & evidence

ORD record
ord-f6449bbd1a8743d28a61c7dbbe24dece
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

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