Propylamine → HCID 69221663, compound

HRID 902052Notes

Reaction equation

HRID 902052 reaction equation
[O:1]=[C:2]1[N:8]([O:9][CH2:10][CH:11]=[CH2:12])[CH:7]2[CH2:13][N:3]1[N:4]([CH2:18][C:19](O)=[O:20])[C:5]1[CH:17]=[CH:16][CH:15]=[CH:14][C:6]=12.O.O[N:24]1[C:28]2C=CC=[CH:32][C:27]=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N)CC>CN(C=O)C.CCCCCCC.CCOC(C)=O>[O:1]=[C:2]1[N:8]([O:9][CH2:10][CH:11]=[CH2:12])[CH:7]2[CH2:13][N:3]1[N:4]([CH2:18][C:19]([NH:24][CH2:28][CH2:27][CH3:32])=[O:20])[C:5]1[CH:17]=[CH:16][CH:15]=[CH:14][C:6]=12

Participants

7

Reactant 4

HCID 7852PropylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 69220293HCID 69220293, compound

Product 1

HCID 69221663HCID 69221663, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21899848Ethylacetate heptaneSolvent

Procedure

480 mg of the acid obtained in Example 25 are dissolved in 5 ml of DMF. 336.5 mg of 1-hydroxybenzotriazole hydrate and then 350 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride are added at 0° C. After 20 min at 0° C., 107.9 g of propylamine are added and then the mixture is left at 0° C. for 20 min. The reaction medium is treated with a heptane/AcOEt (1:2) mixture and NaH2SO4 (1M aqueous solution). After extracting with AcOEt and then washing the organic phase with water, the organic phase is dried over MgSO4 and the solvent is evaporated. The residue is chromatographed on silica (eluent: CH2Cl2; 6% acetone). 207 mg of the expected product (38%) are isolated.

Workup

  1. waitthe mixture is left at 0° C. for 20 min
  2. extractionAfter extracting with AcOEt
  3. washwashing the organic phase with water
  4. dry with materialthe organic phase is dried over MgSO4
  5. customthe solvent is evaporated
  6. customThe residue is chromatographed on silica (eluent: CH2Cl2; 6% acetone)

Sources & evidence

ORD record
ord-4b8cbeb0d0594f4ebd983628f397706a
Source dataset
uspto-grants-2008_04
Patent number
US07365071B2

Reaction notes

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