Formaldehyde → HCID 23630273, compound

HRID 643730Notes

Reaction equation

HRID 643730 reaction equation
[CH:1]([C@:4]1([C:15]([N:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][N:24]=3)[CH2:19][CH2:18]2)=[O:16])[CH2:8][CH2:7][C@@H:6]([NH:9][CH:10]2[CH2:14][CH2:13][O:12][CH2:11]2)[CH2:5]1)([CH3:3])[CH3:2].C=O.[BH3-][C:36]#N.[Na+]>CO>[CH:1]([C@:4]1([C:15]([N:17]2[CH2:18][CH2:19][N:20]([C:23]3[CH:28]=[C:27]([C:29]([F:32])([F:30])[F:31])[CH:26]=[CH:25][N:24]=3)[CH2:21][CH2:22]2)=[O:16])[CH2:8][CH2:7][C@@H:6]([N:9]([CH3:36])[CH:10]2[CH2:14][CH2:13][O:12][CH2:11]2)[CH2:5]1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 23630272HCID 23630272, compound

Product 1

HCID 23630273HCID 23630273, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-[(1R,3S)-3-isopropyl-3-({4-[4-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl}carbonyl)cyclopentyl]tetrahydrofuran-3-amine (160 mg) in 5mL of methanol was added a solution of formaldehyde (10 equiv) followed by NaCNBH3 (3 equiv). Once the reaction was complete, the volatiles were removed and the residue taken in ethyl acetate. The ethyl acetate layer was washed with aqueous NaOH (2.5N). The organic layer was dried over sodium sulfate, filtered and evaporated. The residue was purified by chromatography to give the title compound (126 mg). MS calculated for C24H35F3N4O2: (M+H) 469.2712; found 469.2817.

Workup

  1. customthe volatiles were removed
  2. washThe ethyl acetate layer was washed with aqueous NaOH (2.5N)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-c40932b66b4941b09f87cfdd696fc6aa
Source dataset
uspto-grants-2010_04
Patent number
US07700624B2

Reaction notes

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