Diisopropylethylamine → HCID 21193444, compound

HRID 1068501Notes

Reaction equation

HRID 1068501 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][CH:10]([NH2:13])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:14]([C:16]1[CH:31]=[CH:30][C:19]([CH2:20][N:21]2[C:25](CC([O-])=O)=[CH:24][N:23]=[CH:22]2)=[CH:18][CH:17]=1)#[N:15].[Li+].[OH2:33].ON1C2C=CC=[CH:43][C:38]=2N=N1.[ClH:44].CN(C)CCCN=C=NCC.C(N(CC)C(C)C)(C)C>>[ClH:44].[C:14]([C:16]1[CH:17]=[CH:18][C:19]([CH2:20][N:21]2[CH:25]=[CH:24][N:23]([CH2:38][C:43]([NH:13][CH:10]3[CH2:9][CH2:8][N:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH2:12][CH2:11]3)=[O:33])[CH2:22]2)=[CH:30][CH:31]=1)#[N:15]

Participants

6

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 211933471-Phenylpiperidin-4-amineHCID 67586058HCID 67586058, compound

Product 1

HCID 21193444HCID 21193444, compound

Procedure

1-Phenylpiperidin-4-ylamine (40 mg, 0.227 mmol), lithium [3-(4-cyanobenzyl)-3H-imidazol-4-yl]acetate (56 mg, 0.227 mmol), 1-hydroxybenzotriazole hydrate (46 mg, 0.34 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (87 mg, 0.45 mmol), and N,N-diisopropylethylamine (99 μL, 0.57 mmol) were added to degassed DMF (2 mL) and the mixture was stirred for 18 hrs at room temperature then concentrated in vacuo. The residue was added to sat. NaHCO3(aq) (5 mL) and extracted with dichloromethane (3×3 mL). The combined organic extracts were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was chromatographed on silica gel, eluting with dichloromethane—5% methanol—0.05% NH4OH to give the product as a free base. This was lyophilized from HCl (aq)—acetonitrile to give the title compound as a white solid.

Workup

  1. customto degassed DMF (2 mL)
  2. concentrationthen concentrated in vacuo
  3. additionThe residue was added to sat. NaHCO3(aq) (5 mL)
  4. extractionextracted with dichloromethane (3×3 mL)
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was chromatographed on silica gel
  9. washeluting with dichloromethane—5% methanol—0.05% NH4OH
  10. customto give the product as a free base

Sources & evidence

ORD record
ord-148ccbbc3e084f878080c87cfcfaec42
Source dataset
uspto-grants-2001_06
Patent number
US06248756B1

Reaction notes

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