1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 89852361, compound

HRID 1746899Notes

Reaction equation

HRID 1746899 reaction equation
Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[O:24]1[CH2:29][CH2:28][N:27]([CH2:30][C:31]2[CH:35]=[CH:34][N:33]([C:36]3[N:44]=[CH:43][CH:42]=[CH:41][C:37]=3[C:38]([OH:40])=O)[N:32]=2)[CH2:26][CH2:25]1.[NH2:45][CH:46]([CH2:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)[CH:47]([OH:51])[C:48]([NH2:50])=[O:49]>C(Cl)Cl.CCN(CC)CC>[NH2:50][C:48](=[O:49])[CH:47]([OH:51])[CH:46]([NH:45][C:38](=[O:40])[C:37]1[CH:41]=[CH:42][CH:43]=[N:44][C:36]=1[N:33]1[CH:34]=[CH:35][C:31]([CH2:30][N:27]2[CH2:26][CH2:25][O:24][CH2:29][CH2:28]2)=[N:32]1)[CH2:52][C:53]1[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=1

Participants

7

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 138823553-Amino-2-hydroxy-4-phenylbutanamideHCID 89852072HCID 89852072, compound

Product 1

HCID 89852361HCID 89852361, compoundYield 76.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent2×

Conditions

Temperature
5 °C

Procedure

N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC) (280 mg, 1.461 mmol mmol), 1-hydroxybenzotriazole hydrate (220 mg, 1.437 mmol) and triethylamine (Et3N) (2204) were successively added to a suspension of 2-(3-(morpholinomethyl)-1H-pyrazol-1-yl)nicotinic acid (350 mg, 1.214 mmol) and 3-amino-2-hydroxy-4-phenylbutanamide (260 mg, 1.339 mmol) in CH2Cl2 (40 mL) at 5° C., and the mixture was stirred at 5° C. for about 5 minutes. A pH of 8 was adjusted by adding 50 μL of Et3N, the mixture stirred for 1 hour at 5° C. and then overnight at room temperature. Dichloromethane (50 mL) was added, washed subsequently with water and brine, dried (MgSO4) and concentrated in vacuo to give 430 mg of a yellow oil, which was purified by chromatography over silica gel (eluent CH2Cl2/methanol) to give 260 mg of an amorphous white solid; ESI-MS [M+H]+: 465.2

Workup

  1. stirringthe mixture stirred for 1 hour at 5° C.
  2. customovernight
  3. customat room temperature
  4. washwashed subsequently with water and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2ac8725d09c145dd92d935262afb2465
Source dataset
uspto-grants-2015_10
Patent number
US09150545B2

Reaction notes

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