Triethylamine → Ammonia

HRID 2118045Notes

Reaction equation

HRID 2118045 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-6623edc45b674daaa0d660744f4763c4
Source dataset
uspto-grants-2008_10
Patent number
US07442795B2

Reaction notes

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