1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 67540385, compound

HRID 1400216Notes

Reaction equation

HRID 1400216 reaction equation
Cl.C[N:3](C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[NH:24]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[N:26]=[C:25]1[C:33]1[N:41]=[CH:40][CH:39]=[CH:38][C:34]=1[C:35]([OH:37])=O.N[CH:43]([CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)[CH:44]([OH:48])[C:45]([NH2:47])=[O:46]>ClCCl.CCN(CC)CC>[NH2:47][C:45](=[O:46])[CH:44]([OH:48])[CH:43]([C:40]1[CH:39]=[CH:38][C:34]([C:35]([NH2:3])=[O:37])=[C:33]([C:25]2[NH:24][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[N:26]=2)[N:41]=1)[CH2:49][C:50]1[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=1

Participants

7

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 138823553-Amino-2-hydroxy-4-phenylbutanamideHCID 67539520HCID 67539520, compound

Product 1

HCID 67540385HCID 67540385, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent2×

Conditions

Temperature
5 °C

Procedure

0.2 g N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC), 1.04 g 1-hydroxybenzotriazole hydrate and 150 μL triethylamine (Et3N) were successively added to a solution of 2-(1H-benzo[d]imidazol-2-yl)nicotinic acid (0.2 g. 0.836 mmol) and 3-amino-2-hydroxy-4-phenylbutanamide (170 mg, 0.875 mmol) in 40 ml of dichloromethane at 5° C., and the mixture was stirred at 5° C. for about 5 minutes. A pH of 8-9 was adjusted by adding of 50 μl Et3N, the mixture stirred for 1 hour at 5° C. and then overnight at room temperature. For work up the reaction mixture was evaporated to dryness, treated with 50 ml of water, the precipitate filtered off with suction, washed three times with water and dried at 50° C. over night. The crude product was purified by crystallization from 10 ml of 2-propanole yielding 50 mg of the title compound as white amorphous solid.

Workup

  1. stirringthe mixture stirred for 1 hour at 5° C.
  2. customovernight
  3. customat room temperature
  4. customFor work up the reaction mixture was evaporated to dryness
  5. additiontreated with 50 ml of water
  6. filtrationthe precipitate filtered off with suction
  7. washwashed three times with water
  8. customdried at 50° C. over night
  9. customThe crude product was purified by crystallization from 10 ml of 2-propanole yielding 50 mg of the title compound as white amorphous solid

Sources & evidence

ORD record
ord-51d939e88c7840508ce9e27046d34649
Source dataset
uspto-grants-2014_12
Patent number
US08906941B2

Reaction notes

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