Formaldehyde → N-(2-{(1S,2S)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethyl)-N-methyl-4-(methylsulfonyl)aniline

HRID 1039060Notes

Reaction equation

HRID 1039060 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([C@H:14]3[CH2:16][C@H:15]3[CH2:17][CH2:18][NH:19][C:20]3[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][CH:21]=3)[CH2:10][CH2:9]2)=[N:6][CH:7]=1.C=O.Cl[CH:33](Cl)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([C@H:14]3[CH2:16][C@H:15]3[CH2:17][CH2:18][N:19]([CH3:33])[C:20]3[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][CH:21]=3)[CH2:10][CH2:9]2)=[N:6][CH:7]=1

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 63651,1-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 67778566HCID 67778566, compound

Product 1

HCID 50939661N-(2-{(1S,2S)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethyl)-N-methyl-4-(methylsulfonyl)aniline

Procedure

N-(2-{(1S,2S)-2-[1-(5-chloropyrimidin-2-yl)piperidin-4-yl]cyclopropyl}ethyl)-4-(methylsulfonyl)aniline (6 mg, 0.014 mmol) from Example 7 and paraformaldehyde were added to dichloroethane (0.2 mL), then sodium triacetoxyborohydride (10.1 mg, 0.041 mmol) was added and stirred overnight at room temperature. The reaction was quenched with sodium bicarbonate saturated solution (10 mL), extracted with EtOAc (10 mL), second wash with Brine (10 mL). The organic phase was dried by magnesium sulfate, filtered, concentrated and purified by purified by preparative-TLC (Analtech Silica Gel GF 1500 μM, 20×20 cm) using 50% ethyl acetate/hexane to give the title compound as a white solid.

Workup

  1. customThe reaction was quenched with sodium bicarbonate saturated solution (10 mL)
  2. extractionextracted with EtOAc (10 mL)
  3. washsecond wash with Brine (10 mL)
  4. dry with materialThe organic phase was dried by magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified
  8. customby purified by preparative-TLC (Analtech Silica Gel GF 1500 μM, 20×20 cm)

Sources & evidence

ORD record
ord-fd9b1fac8dfd4199a90f7bfe1695197d
Source dataset
uspto-grants-2013_10
Patent number
US08552022B2

Reaction notes

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