Cyclopropanemethanamine → HCID 86671005, compound

HRID 515386Notes

Reaction equation

HRID 515386 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH:11]2[CH2:16][CH2:15][N:14]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([OH:33])([C:29]([F:32])([F:31])[F:30])[C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=3)[CH2:13][CH2:12]2)=[CH:4][CH:3]=1.[C:34](Cl)(=O)[O:35]C1C=CC([N+]([O-])=O)=CC=1.[CH:47]1([CH2:50][NH2:51])[CH2:49][CH2:48]1>O1CCCC1>[CH:47]1([CH2:50][NH:51][C:34]([NH:1][C:2]2[CH:10]=[C:9]3[C:5]([CH:6]=[CH:7][N:8]3[CH:11]3[CH2:12][CH2:13][N:14]([CH2:17][C:18]4[CH:19]=[CH:20][C:21]([C:24]([OH:33])([C:29]([F:32])([F:31])[F:30])[C:25]([F:26])([F:27])[F:28])=[CH:22][CH:23]=4)[CH2:15][CH2:16]3)=[CH:4][CH:3]=2)=[O:35])[CH2:49][CH2:48]1

Participants

5

Reactant 3

HCID 75646CyclopropanemethanamineHCID 821294-Nitrophenyl chloroformateHCID 86671006HCID 86671006, compound

Product 1

HCID 86671005HCID 86671005, compoundYield 12.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-((4-(6-Amino-1H-indol-1-yl)piperidin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (0.350 mmol, 0.165 g) and 4-nitrophenyl carbonochloridate (0.350 mmol, 0.071 g) were combined and stirred in tetrahydrofuran (2 mL) for 1 hour. Cyclopropylmethanamine (0.700 mmol, 0.061 mL, 0.050 g) was added and the reaction stirred at room temperature for 2 hours. The organic phase was washed with water and dried over sodium sulfate. The solvent was removed and the resulting residue was purified by silica chromatography (eluting with a solvent gradient from dichloromethane to 3% methanol/dichloromethane) to afford the title compound (24 mg). MS (ESI) m/z 569.2 [M+H]+

Workup

  1. washThe organic phase was washed with water
  2. dry with materialdried over sodium sulfate
  3. customThe solvent was removed
  4. customthe resulting residue was purified by silica chromatography (
  5. washeluting with a solvent gradient from dichloromethane to 3% methanol/dichloromethane)

Sources & evidence

ORD record
ord-886e7964b9aa428cb940d34f0e80b9cb
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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