1,2-Dichloroethane → 4-[1-(5-Methylcarbamoyl-4-trifluoromethyl-pyrimidin-2-yl)-piperidin-4-ylideneaminooxy]-piperidine-1-carboxylic acid isopropyl ester

HRID 2066875Notes

Reaction equation

HRID 2066875 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[N:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[C:24]([C:31](O)=[O:32])=[CH:23][N:22]=3)[CH2:17][CH2:16]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].CN.C1C=CC2N(O)N=[N:42][C:40]=2C=1.C(Cl)CCl>C(Cl)Cl>[CH:1]([O:4][C:5]([N:7]1[CH2:8][CH2:9][CH:10]([O:13][N:14]=[C:15]2[CH2:16][CH2:17][N:18]([C:21]3[N:26]=[C:25]([C:27]([F:30])([F:28])[F:29])[C:24]([C:31](=[O:32])[NH:42][CH3:40])=[CH:23][N:22]=3)[CH2:19][CH2:20]2)[CH2:11][CH2:12]1)=[O:6])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 6329MethylamineHCID 757711-HydroxybenzotriazoleHCID 866550162-[4-(1-Isopropoxycarbonyl-piperidin-4-yloxyimino)-piperidin-1-yl]-4-trifluoromethyl-pyrimidine-5-carboxylic acid

Product 1

HCID 866550174-[1-(5-Methylcarbamoyl-4-trifluoromethyl-pyrimidin-2-yl)-piperidin-4-ylideneaminooxy]-piperidine-1-carboxylic acid isopropyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Half of the crude 57b was combined with methylamine (0.06 mmol), HOBT (7 mg, 0.06 mmol) and EDC(10 mg, 0.05 mmol) in 1 mL of DCM. The mixture was stirred at room temperature for 18 h, washed with aqueous NaHCO3 and concentrated. The residue was purified by preparative HPLC to afford 57-1: LC-MS 487.3 (MH+), tR=5.20 (Method 5).

Workup

  1. washwashed with aqueous NaHCO3
  2. concentrationconcentrated
  3. customThe residue was purified by preparative HPLC
  4. customto afford 57-1

Sources & evidence

ORD record
ord-cef2885383484c7bbfc1ace5ddc6e02d
Source dataset
uspto-grants-2012_10
Patent number
US08293729B2

Reaction notes

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