Methyl chloroformate → HCID 58852295, compound

HRID 1716598Notes

Reaction equation

HRID 1716598 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6]([CH2:11][N:12]1[CH2:17][CH2:16][CH:15]([N:18]3[C:22]4[CH:23]=[CH:24][C:25]([CH3:27])=[CH:26][C:21]=4[N:20]=[C:19]3[C:28]([OH:31])([CH3:30])[CH3:29])[CH2:14][CH2:13]1)[CH2:5]2.C(N(CC)C(C)C)(C)C.Cl[C:42]([O:44][CH3:45])=[O:43]>C1COCC1>[CH3:45][O:44][C:42](=[O:43])[NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6]([CH2:11][N:12]1[CH2:13][CH2:14][CH:15]([N:18]3[C:22]4[CH:23]=[CH:24][C:25]([CH3:27])=[CH:26][C:21]=4[N:20]=[C:19]3[C:28]([OH:31])([CH3:29])[CH3:30])[CH2:16][CH2:17]1)[CH2:5]2

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 68511631HCID 68511631, compound

Product 1

HCID 58852295HCID 58852295, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-{1-[1-(5-amino-indan-2-ylmethyl)-piperidin-4-yl]-5-methyl-1H-benzoimidazol-2-yl}-propan-2-ol (36 mg, 0.096 mmol), N,N-diisopropylethylamine (37 mg, 0.29 mmol) in THF (3 mL) was added methyl chloroformate (9 mg, 0.11 mmol). After stirring overnight, the reaction mixture was quenched with silica-supported diamine-3 (95 mg, Silicycle) to scavenge the excessive amount of methyl chloroformate. The mixture was filtered and concentrated in vacuo, and the residue was purified by flash chromatography eluent to afford (2-{4-[2-(1-hydroxy-1-methyl-ethyl)-5-methyl-benzoimidazol-1-yl]-piperidin-1-ylmethyl}-indan-5-yl)-carbamic acid methyl ester (20 mg, 59%) as white solid.

Workup

  1. customthe reaction mixture was quenched with silica-supported diamine-3 (95 mg, Silicycle)
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated in vacuo
  4. customthe residue was purified by flash chromatography eluent

Sources & evidence

ORD record
ord-f783cc4a94d94bffa0af206db9c3f339
Source dataset
uspto-grants-2010_09
Patent number
US07803816B2

Reaction notes

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