Triethylamine → Ammonia

HRID 1243590Notes

Reaction equation

HRID 1243590 reaction equation
Cl.C[N:3](C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[CH3:31][O:32][CH2:33][CH2:34][C:35]([OH:37])=O.[Cl:38][C:39]1[CH:64]=[CH:63][C:42]2[N:43]3[C:47]([CH2:48][NH:49][CH2:50][C:41]=2[CH:40]=1)=[N:46][N:45]=[C:44]3[CH:51]1[CH2:56][CH2:55][N:54]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][N:58]=2)[CH2:53][CH2:52]1>ClCCl>[NH3:3].[Cl:38][C:39]1[CH:64]=[CH:63][C:42]2[N:43]3[C:47]([CH2:48][N:49]([C:35](=[O:37])[CH2:34][CH2:33][O:32][CH3:31])[CH2:50][C:41]=2[CH:40]=1)=[N:46][N:45]=[C:44]3[CH:51]1[CH2:52][CH2:53][N:54]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][N:58]=2)[CH2:55][CH2:56]1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 1344423-Methoxypropionic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 113264888-Chloro-1-(3,4,5,6-tetrahydro-2h-[1,2']bipyridinyl-4-yl)-5,6-dihydro4h-2,3,5,10b-tetraaza-benzo[e]azulene

Product 2

HCID 222AmmoniaHCID 21925599HCID 21925599, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (116 mg, 0.6 mmol) followed by 1-hydroxybenzotriazole hydrate (81 mg, 0.6 mmol) and triethylamine (84 μl, 0.6 mmol) were added to a solution of 3-methoxypropionic acid (63 mg, 0.6 mmol) in dichloromethane (10 ml) and the solution stirred for 10 minutes. The amine from example 4 (150 mg, 0.4 mmol) was added and the reaction stirred at room temperature for 5 hours. The reaction was washed with saturated sodium bicarbonate solution, dried over magnesium sulphate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using dichloromethane:methanol:0.88 ammonia (95:5:0.5) to give the title compound as a white solid, 166 mg.

Workup

  1. stirringthe reaction stirred at room temperature for 5 hours
  2. washThe reaction was washed with saturated sodium bicarbonate solution
  3. dry with materialdried over magnesium sulphate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-6c5e75661220418485ab35c348e6795c
Source dataset
uspto-grants-2006_10
Patent number
US07119088B2

Reaction notes

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