Dimethylamine, hydrochloride → HCID 89714575, compound

HRID 2273068Notes

Reaction equation

HRID 2273068 reaction equation
[CH2:1]([NH:3][C:4](=[O:39])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:22]3[C:21](=[O:23])[N:20]([CH2:24][CH2:25][C:26](O)=[O:27])[CH2:19][C:18]([CH3:30])([CH3:29])[O:17][C:16]=3[N:15]=[C:14]([N:31]3[CH2:37][CH:36]4[O:38][CH:33]([CH2:34][CH2:35]4)[CH2:32]3)[N:13]=2)=[CH:8][CH:7]=1)[CH3:2].C[CH2:41][N:42](C(C)C)[CH:43](C)C.Cl.CNC.OC1C2N=NNC=2C=CC=1.Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl.C(#N)C>[CH2:1]([NH:3][C:4](=[O:39])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:22]3[C:21](=[O:23])[N:20]([CH2:24][CH2:25][C:26]([N:42]([CH3:43])[CH3:41])=[O:27])[CH2:19][C:18]([CH3:30])([CH3:29])[O:17][C:16]=3[N:15]=[C:14]([N:31]3[CH2:37][CH:36]4[O:38][CH:33]([CH2:34][CH2:35]4)[CH2:32]3)[N:13]=2)=[CH:8][CH:7]=1)[CH3:2]

Participants

8

Reactant 5

HCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 89714824HCID 89714824, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 89714575HCID 89714575, compoundYield 46.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

70 mg (0.13 mmol) of 3-[4-[4-(3-ethylureido)phenyl]-8,8-dimethyl-2-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-5-oxo-7,8-dihydro-5H-9-oxa-1,3,6-triazabenzocyclohepten-6-yl]propionic acid are placed in 3 ml of DCM. 0.66 ml of DIEA (0.39 mmol), 12 mg of dimethylamine hydrochloride (0.14 mmol), 21 mg of hydroxybenzotriazole (0.14 mmol) and 27 mg of 1-ethyl-3-(dimethylaminopropyl)carbodiimide hydrochloride (0.14 mmol) are successively added, with stirring. After stirring for 3 days at room temperature, the DCM is evaporated off. The residue is taken up in water and extracted with ethyl acetate. The organic phase is washed with saturated aqueous NaHCO3 solution and then with brine, dried over MgSO4, filtered and evaporated. The solid obtained is taken up in acetonitrile, filtered off and rinsed with pentane to give 34 mg of 3-[4-[4-(3-ethylureido)phenyl]-8,8-dimethyl-2-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-5-oxo-7,8-dihydro-5H-9-oxa-1,3,6-triazabenzocyclohepten-6-yl]-N,N-dimethylpropionamide.

Workup

  1. stirringAfter stirring for 3 days at room temperature
  2. customthe DCM is evaporated off
  3. extractionextracted with ethyl acetate
  4. washThe organic phase is washed with saturated aqueous NaHCO3 solution
  5. dry with materialwith brine, dried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe solid obtained
  9. filtrationfiltered off
  10. washrinsed with pentane

Sources & evidence

ORD record
ord-1195b551c777466093b2b2b1721124a8
Source dataset
uspto-grants-2015_09
Patent number
US09120812B2

Reaction notes

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