Formaldehyde → HCID 11225377, compound

HRID 1592348Notes

Reaction equation

HRID 1592348 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[C:9]([NH:13][C:14]([NH:16][CH2:17][C@@H:18]3[CH2:23][CH2:22][CH2:21][CH2:20][C@H:19]3[NH:24][CH2:25][CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)=[O:15])[CH:10]=[CH:11][CH:12]=2)=[N:5][N:4]=[N:3]1.C=O.[C:37]([BH3-])#N.[Na+]>C(Cl)Cl.C1COCC1>[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[C:9]([NH:13][C:14]([NH:16][CH2:17][C@@H:18]3[CH2:23][CH2:22][CH2:21][CH2:20][C@H:19]3[N:24]([CH2:25][CH2:26][CH2:27][C:28]3[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=3)[CH3:37])=[O:15])[CH:10]=[CH:11][CH:12]=2)=[N:5][N:4]=[N:3]1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 11317248HCID 11317248, compound

Product 1

HCID 11225377HCID 11225377, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[3-(1-methyl-tetrazol-5-yl)phenyl]-N′-[(1S,2R)-2-[3-(4-fluorophenyl)propylamino]-cyclohexylmethyl]urea (98 mg), the product of Step g of Example 31, in 4 mL of CH2Cl2 was added a solution of formaldehyde in THF (excess), and the mixture was stirred for 15 minutes. Then excess amount of sodium cyanoborohydride was added, and the mixture was continued to stir for 5 hrs at room temperature. After quenching the reaction with saturated Na2CO3, it was extracted with CH2Cl2. The extract was washed with water, dried over MgSO4 and evaporated to give an oily residue. It was purified by column chromatography (silica gel, 0.6:5.494 cNH4OH/CH3OH/CH2Cl2) to give pure N-[3-(1-methyl-tetrazol-5-yl)phenyl]-N′-[(1S,2R)-2-[N-methyl-3-(4-fluorophenyl)propylamino]-cyclohexylmethyl]urea.

Workup

  1. stirringto stir for 5 hrs at room temperature
  2. customAfter quenching
  3. customthe reaction with saturated Na2CO3, it
  4. extractionwas extracted with CH2Cl2
  5. washThe extract was washed with water
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customto give an oily residue
  9. customIt was purified by column chromatography (silica gel, 0.6:5.494 cNH4OH/CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-bcaccc71775a4103b2ad4046532c131d
Source dataset
uspto-grants-2007_11
Patent number
US07291744B2

Reaction notes

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