Triethylamine → HCID 58012133, compound

HRID 660921Notes

Reaction equation

HRID 660921 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([C:9]2([NH2:13])[CH2:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.C(N(CC)CC)C.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[N:32]([CH:33]3[CH2:35][CH2:34]3)[C:31](=[O:36])[N:30]([CH2:37][C:38](O)=[O:39])[N:29]=2)=[CH:24][CH:23]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C)C=O>[Cl:2][C:3]1[CH:4]=[C:5]([C:9]2([NH:13][C:38](=[O:39])[CH2:37][N:30]3[C:31](=[O:36])[N:32]([CH:33]4[CH2:34][CH2:35]4)[C:28]([C:25]4[CH:26]=[CH:27][C:22]([Cl:21])=[CH:23][CH:24]=4)=[N:29]3)[CH2:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 42632357[3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetic acidHCID 532569491-(3-Chlorophenyl)cyclobutan-1-amine--hydrogen chloride (1/1)

Product 1

HCID 58012133HCID 58012133, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

57.2 mg (0.262 mmol) of 1-(3-chlorophenyl)cyclobutanamine hydrochloride are placed in 2 ml of dimethylformamide and treated with 26.5 mg (0.262 mmol) of triethylamine. After 10 mins' stirring, 70.0 mg (0.238 mmol) of [3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetic acid from Example 88A and 38.7 mg (0.286 mmol) of HOBt are added. After a further 10 mins' stirring, the mixture is treated with 59.4 mg (0.310 mmol) of EDC hydrochloride and stirred overnight at room temperature. For the workup, the reaction mixture is partitioned between dichloromethane and water, and the organic phase is separated, dried over sodium sulphate and concentrated. The residue is purified by flash chromatography on silica gel (eluent: dichloromethane/methanol first 200:1, then 100:1) and thus yields 66 mg (61% of theory) of the target compound.

Workup

  1. stirringAfter a further 10 mins' stirring
  2. stirringstirred overnight at room temperature
  3. customFor the workup, the reaction mixture is partitioned between dichloromethane and water
  4. customthe organic phase is separated
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. customThe residue is purified by flash chromatography on silica gel (eluent

Sources & evidence

ORD record
ord-1d73eaaa6ac346fe9ee4ca648c6bf422
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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