Trimethyl orthoformate → 4-[1-(6-Fluoro-3H-benzoimidazol-5-yl)-piperidin-4-ylideneaminooxy]-piperidine-1-carboxylic acid isopropyl ester

HRID 2066881Notes

Reaction equation

HRID 2066881 reaction equation
[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][N:14]=[C:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[C:25]([NH2:27])[C:24]([NH2:28])=[CH:23][C:22]=3[F:29])[CH2:17][CH2:16]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].[CH3:30]C1C=CC(S(O)(=O)=O)=CC=1.O.C(OC)(OC)OC>CN(C=O)C>[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][N:14]=[C:15]2[CH2:20][CH2:19][N:18]([C:21]3[C:22]([F:29])=[CH:23][C:24]4[N:28]=[CH:30][NH:27][C:25]=4[CH:26]=3)[CH2:17][CH2:16]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 9005Trimethyl orthoformateHCID 521998p-Toluenesulfonic acid monohydrateHCID 866550204-[1-(4,5-Diamino-2-fluoro-phenyl)-piperidin-4-ylideneaminooxy]-piperidine-1-carboxylic acid isopropyl ester

Product 1

HCID 1784597094-[1-(6-Fluoro-3H-benzoimidazol-5-yl)-piperidin-4-ylideneaminooxy]-piperidine-1-carboxylic acid isopropyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The crude 60b was combined with TsOH.H2O (50 mg) in 2 mL of DMF and treated with HC(OMe)3 (1 mL). The mixture was stirred for 16 h then concentrated and purified on preparative HPLC to afford 60-1: LC-MS 418.4 (MH+), tR=4.64 (Method 4).

Workup

  1. concentrationthen concentrated
  2. custompurified on preparative HPLC
  3. customto afford 60-1

Sources & evidence

ORD record
ord-24bb4971e08f4622bc8c4475436b349e
Source dataset
uspto-grants-2012_10
Patent number
US08293729B2

Reaction notes

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