Diisopropylethylamine → 4-[5-(2-Fluoro-4-methanesulfonyl-phenyl)-furo[2,3-c]pyridin-2-yl]-piperidine-1-carboxylic acid 1-methyl-cyclopropyl ester

HRID 1471792Notes

Reaction equation

HRID 1471792 reaction equation
[C:1](=[O:17])(OC1C=CC([N+]([O-])=O)=CC=1)[O:2][C:3]1([CH3:6])[CH2:5][CH2:4]1.[F:18][C:19]1[CH:24]=[C:23]([S:25]([CH3:28])(=[O:27])=[O:26])[CH:22]=[CH:21][C:20]=1[C:29]1[CH:30]=[C:31]2[CH:37]=[C:36]([CH:38]3[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]3)[O:35][C:32]2=[CH:33][N:34]=1.C(N(CC)C(C)C)(C)C>O1CCCC1>[CH3:6][C:3]1([O:2][C:1]([N:41]2[CH2:42][CH2:43][CH:38]([C:36]3[O:35][C:32]4=[CH:33][N:34]=[C:29]([C:20]5[CH:21]=[CH:22][C:23]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:24][C:19]=5[F:18])[CH:30]=[C:31]4[CH:37]=3)[CH2:39][CH2:40]2)=[O:17])[CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 579301151-Methylcyclopropyl 4-nitrophenyl carbonateHCID 866945755-(2-Fluoro-4-methanesulfonyl-phenyl)-2-piperidin-4-yl-furo[2,3-c]pyridine

Product 1

HCID 717367244-[5-(2-Fluoro-4-methanesulfonyl-phenyl)-furo[2,3-c]pyridin-2-yl]-piperidine-1-carboxylic acid 1-methyl-cyclopropyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Methyl-cyclopropyl 4-nitrophenyl carbonate (48 mg) is added to a solution of 5-(2-fluoro-4-methanesulfonyl-phenyl)-2-piperidin-4-yl-furo[2,3-c]pyridine (75 mg) and N,N-diisopropyl-ethylamine (32 μL) in tetrahydrofuran (1 mL) at room temperature. The mixture is stirred at room temperature overnight. The solution is concentrated and the residue is taken up in ethyl acetate. The resulting mixture is washed with 1 M aqueous NaOH solution (3×), water, and brine. The organic phase is dried (Na2SO4) and concentrated. The residue is purified by HPLC on reversed phase (methanol/water) to give the title compound. Mass spectrum (ESI+): m/z=473 [M+H]+.

Workup

  1. concentrationThe solution is concentrated
  2. washThe resulting mixture is washed with 1 M aqueous NaOH solution (3×), water, and brine
  3. dry with materialThe organic phase is dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue is purified by HPLC on reversed phase (methanol/water)

Sources & evidence

ORD record
ord-64e431bc24704ea88cdd91832ab2150b
Source dataset
uspto-grants-2015_04
Patent number
US09012456B2

Reaction notes

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