Diisopropylethylamine → HCID 131723694, compound

HRID 2298089Notes

Reaction equation

HRID 2298089 reaction equation
C(N(C(C)C)C(C)C)C.[Cl:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][C:12]=1[C:20]([NH:22][CH2:23][C:24]12[CH2:33][CH:28]3[CH2:29][CH:30]([CH2:32][CH:26]([CH2:27]3)[CH2:25]1)[CH2:31]2)=[O:21].C(OC([N:41]1[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1)=O)(C)(C)C.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN1CCCC1=O.C(OCC)(=O)C>[ClH:10].[Cl:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([N:41]2[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]2)=[O:17])=[CH:13][C:12]=1[C:20]([NH:22][CH2:23][C:24]12[CH2:31][CH:30]3[CH2:29][CH:28]([CH2:27][CH:26]([CH2:32]3)[CH2:25]1)[CH2:33]2)=[O:21]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 2733179PyBroPHCID 18381486HCID 18381486, compound

Product 1

HCID 131723694HCID 131723694, compoundYield 102.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Ethyldiisopropylamine (0.3 ml) was added at ambient temperature to a solution of 4-chloro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-isophthalamic acid (0.15 g, Example 60a), piperazine-1-carboxylic acid tert-butyl ester (0.16 g) and PyBrOP (0.40 g) in N-methylpyrrolidinone (10 ml). After 5 h the reaction mixture was diluted with ethyl acetate and washed twice with water, twice with 10% KHSO4 solution, twice with saturated NaHCO3 solution and once with brine, then dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (eluting with ethanol (0-5%) in dichloromethane), then redissolved in methanol (10 ml) and treated with hydrochloric acid (4N dioxane, 1 ml). After 48 h the reaction mixture was concentrated under reduced pressure and recrystallised from iso-hexaxne/propan-2-ol to yield the title compound as a solid (0.10 g).

Workup

  1. washwashed twice with water, twice with 10% KHSO4 solution, twice with saturated NaHCO3 solution and once with brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (eluting with ethanol (0-5%) in dichloromethane)
  5. dissolutionredissolved in methanol (10 ml)
  6. additiontreated with hydrochloric acid (4N dioxane, 1 ml)
  7. concentrationAfter 48 h the reaction mixture was concentrated under reduced pressure
  8. customrecrystallised from iso-hexaxne/propan-2-ol

Sources & evidence

ORD record
ord-65b5fc3665784fc2bd061a82c3c14bfa
Source dataset
uspto-grants-2002_12
Patent number
US06492355B1

Reaction notes

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