Triethylamine → HCID 59333671, compound

HRID 1876552Notes

Reaction equation

HRID 1876552 reaction equation
O.ON1C2C=CC=CC=2N=N1.Cl.CN(CCCN=C=NCC)C.C(N(CC)CC)C.[CH:31]1([CH2:34][N:35]2[C:43]([N:44]3[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]3)=[N:42][C:41]3[C:36]2=[N:37][C:38]([C:56]2[CH:57]=[N:58][C:59]([NH2:62])=[N:60][CH:61]=2)=[N:39][C:40]=3[N:50]2[CH2:55][CH2:54][O:53][CH2:52][CH2:51]2)[CH2:33][CH2:32]1.[N:63]1([CH2:68][C:69](O)=[O:70])[CH:67]=[CH:66][N:65]=[CH:64]1>ClCCl.CO.CN(C)C=O>[CH:31]1([CH2:34][N:35]2[C:43]([N:44]3[CH2:49][CH2:48][N:47]([C:69](=[O:70])[CH2:68][N:63]4[CH:67]=[CH:66][N:65]=[CH:64]4)[CH2:46][CH2:45]3)=[N:42][C:41]3[C:36]2=[N:37][C:38]([C:56]2[CH:61]=[N:60][C:59]([NH2:62])=[N:58][CH:57]=2)=[N:39][C:40]=3[N:50]2[CH2:55][CH2:54][O:53][CH2:52][CH2:51]2)[CH2:32][CH2:33]1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 656129Imidazole-1-acetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 593335735-[9-(Cyclopropylmethyl)-6-morpholin-4-yl-8-piperazin-1-yl-9H-purin-2-yl]pyrimidin-2-amine

Product 1

HCID 59333671HCID 59333671, compoundYield 79.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

1-Hydroxybenzotriazole monohydrate (38.2 mg, 0.25 mmol), 1-(dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (71.8 mg, 0.37 mmol), and triethylamine (52.2 μl, 0.37 mmol) were added to an N,N-dimethylformamide suspension (3.0 ml) of 5-[9-(cyclopropylmethyl)-6-morpholin-4-yl-8-piperazin-1-yl-9H-purin-2-yl]pyrimidin-2-amine (109.0 mg, 0.25 mmol) and imidazol-1-ylacetic acid (37.8 mg, 0.30 mmol) at room temperature. The resulting mixture was stirred for 17.5 hours and the reaction mixture was poured into dichloromethane-methanol (10:1), washed with saturated aqueous sodium hydrogen carbonate solution, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure and the resulting residue was purified by preparative thin layer silica gel chromatography (dichloromethane:methanol=6:1) to give the title compound (108.0 mg, 79%) as a pale yellow solid.

Workup

  1. washwashed with saturated aqueous sodium hydrogen carbonate solution
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customthe resulting residue was purified by preparative thin layer silica gel chromatography (dichloromethane:methanol=6:1)

Sources & evidence

ORD record
ord-aba10ffeee0f4cb19c1ea5f8ff8cddd3
Source dataset
uspto-grants-2012_11
Patent number
US08309546B2

Reaction notes

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