N,N-Dimethylglycine → 2-[1-(1-(N,N-Dimethylaminoacetyl)piperidin-3-yl)-ethylamino]-4-[benzimidazol-1-yl]pyrimidine

HRID 2268963Notes

Reaction equation

HRID 2268963 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH2:2]1.[CH3:25][N:26]([CH3:31])[CH2:27][C:28](O)=[O:29].Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CCOC(C)=O>[CH3:25][N:26]([CH2:27][C:28]([N:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH2:2]1)=[O:29])[CH3:31]

Participants

6

Reactant 3

HCID 673N,N-DimethylglycineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 183326302-[1-(Piperidin-3-yl)-ethylamino]-4-[benzimidazol-1-yl]pyrimidine

Product 1

HCID 207119912-[1-(1-(N,N-Dimethylaminoacetyl)piperidin-3-yl)-ethylamino]-4-[benzimidazol-1-yl]pyrimidine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-[1-(piperidin-3-yl)-ethylamino]-4-[benziniidazol-1-yl]pyrimidine (EXAMPLE 18) (21 mg, 0.065 mmol) in CH2Cl2 (0.6 mL) was added N,N-dimethylglycine (10 mg, 0.098 mmol) followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (19 mg, 0.098 mmol) at room temperature. After stirring for 4.5 h, the reaction mixture was diluted with EtOAc (5 mL) and was washed with H2O (2×2 mL) and brine. The organic layer was dried over Na2SO4. After removal of the solvent, the crude product was purified by preparative thin layer chromatography (1:9 2M NH3 in MeOH:CH2Cl2) to obtain the title compound. Presence of rotamers in Partial 1H NMR (500 MHz, CDCl3): δ 8.6 (s, 1H); 8.35 (br s, 1H); 8.12 (d, J=7.5 Hz, 1H); 7.82 (br s, 1H); 7.35 (br s, 2H); 6.75 (two d, J=5.3 Hz, 1H); 4.54 (m, 1H); 2.24 (s, 3H); 2.19 (s, 3H); 1.28 (br s, 3H). Mass spectrum 408.4 (ESI, M+1).

Workup

  1. washwas washed with H2O (2×2 mL) and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customAfter removal of the solvent
  4. customthe crude product was purified by preparative thin layer chromatography (1:9 2M NH3 in MeOH:CH2Cl2)

Sources & evidence

ORD record
ord-46beffc105ee43b098fd77bc492d92b2
Source dataset
uspto-grants-2001_12
Patent number
US06329380B1

Reaction notes

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