Triethylamine → HCID 45376101, compound

HRID 1876584Notes

Reaction equation

HRID 1876584 reaction equation
[C:1]([OH:6])(=O)[C@H:2]([CH3:4])[OH:3].O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C.[CH:37]1([CH2:40][N:41]2[C:49]([N:50]3[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]3)=[N:48][C:47]3[C:42]2=[N:43][C:44]([C:62]2[CH:63]=[N:64][C:65]([NH2:68])=[N:66][CH:67]=2)=[N:45][C:46]=3[N:56]2[CH2:61][CH2:60][O:59][CH2:58][CH2:57]2)[CH2:39][CH2:38]1>C(Cl)Cl.CO.CN(C)C=O>[NH2:68][C:65]1[N:64]=[CH:63][C:62]([C:44]2[N:43]=[C:42]3[C:47]([N:48]=[C:49]([N:50]4[CH2:51][CH2:52][N:53]([C:1](=[O:6])[C@@H:2]([OH:3])[CH3:4])[CH2:54][CH2:55]4)[N:41]3[CH2:40][CH:37]3[CH2:38][CH2:39]3)=[C:46]([N:56]3[CH2:61][CH2:60][O:59][CH2:58][CH2:57]3)[N:45]=2)=[CH:67][N:66]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 107689L-Lactic 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 45376101HCID 45376101, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

L-Lactic acid (25.2 μl, 0.29 mmol), 1-hydroxybenzotriazole monohydrate (36.7 mg, 0.24 mmol), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (68.8 mg, 0.36 mmol), and triethylamine (50.1 μl, 0.36 mmol) were added to an N,N-dimethylformamide suspension (2.0 ml) of 5-[9-(cyclopropylmethyl)-6-morpholin-4-yl-8-piperazin-1-yl-9H-purin-2-yl]pyrimidin-2-amine (104.5 mg, 0.24 mmol) at room temperature. The resulting mixture was stirred for 17 hours and then the reaction mixture was poured into methylene chloride-methanol (10:1), washed with saturated aqueous sodium hydrogencarbonate 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 (methylene chloride:methanol=10:1) to give the title compound (80.1 mg, 66%) as a pale yellow solid.

Workup

  1. washwashed with saturated aqueous sodium hydrogencarbonate 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 (methylene chloride:methanol=10:1)

Sources & evidence

ORD record
ord-92015ccd816b434893c3befb18ca633c
Source dataset
uspto-grants-2012_11
Patent number
US08309546B2

Reaction notes

Loading…