Diisopropylethylamine → (S)-N-(1-{4-[1-(N-hydroxycarbamimidoyl)-piperidin-4-yl]-phenyl}-ethyl)acetamide

HRID 1470741Notes

Reaction equation

HRID 1470741 reaction equation
Cl.[NH2:2][OH:3].[C:4]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:17]=[CH:16][C:15]([C@@H:18]([NH:20][C:21](=[O:23])[CH3:22])[CH3:19])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)#[N:5].CCN(C(C)C)C(C)C>C(O)C>[OH:3][NH:2][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:13]=[CH:14][C:15]([C@@H:18]([NH:20][C:21](=[O:23])[CH3:22])[CH3:19])=[CH:16][CH:17]=2)[CH2:8][CH2:7]1)=[NH:5]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochloride2×HCID 86666703HCID 86666703, compound

Product 1

HCID 178475062(S)-N-(1-{4-[1-(N-hydroxycarbamimidoyl)-piperidin-4-yl]-phenyl}-ethyl)acetamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

256.4 mg (3.69 mmol) Hydroxylamine hydrochloride are added to a mixture of 1.0 g (3.69 mmol) (S)-N-{1-[4-(1-cyano-piperidin-4-yl)-phenyl]ethyl}-acetamide (XXVII.1) and 0.63 mL (3.69 mmol) DIPEA in 20 mL ethanol. The mixture is refluxed for 4 h, an additional amount of 50 mg hydroxylamine hydrochloride is added and refluxing is continued for 2 h. The solvent is removed in vacuo and water is added. The mixture is then purified by HPLC (RP C18 Xbridge, water (+0.1% ammonia)/MeOH) to yield the desired product.

Workup

  1. temperatureThe mixture is refluxed for 4 h
  2. temperaturerefluxing
  3. customThe solvent is removed in vacuo and water
  4. additionis added
  5. customThe mixture is then purified by HPLC (RP C18 Xbridge, water (+0.1% ammonia)/MeOH)

Sources & evidence

ORD record
ord-15da8e156f4d4a40b43d16ca748ff6b6
Source dataset
uspto-grants-2015_04
Patent number
US09006450B2

Reaction notes

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