Dimethylamine → HCID 58127273, compound

HRID 1623370Notes

Reaction equation

HRID 1623370 reaction equation
[Cl:1][C:2]1[C:3]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([NH:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=3)[N:18]=2)=[CH:4][C:5]([NH:8][C@@H:9]2[CH2:13][CH2:12][C@H:11]([C:14](O)=[O:15])[CH2:10]2)=[N:6][CH:7]=1.[CH3:32][NH:33][CH3:34].C1COCC1.Cl.C(N=C=NCCCN(C)C)C.N1C2C(=NC=CC=2)N(O)N=1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[Cl:1][C:2]1[C:3]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([NH:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=3)[N:18]=2)=[CH:4][C:5]([NH:8][C@@H:9]2[CH2:13][CH2:12][C@H:11]([C:14]([N:33]([CH3:34])[CH3:32])=[O:15])[CH2:10]2)=[N:6][CH:7]=1

Participants

8

Reactant 6

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66936933(1S,3R)-3-(5'-chloro-6-(3-fluorobenzylamino)-2,4'-bipyridin-2'-yl-amino)cyclopentanecarboxylic acid

Product 1

HCID 58127273HCID 58127273, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To (1S,3R)-3-(5′-chloro-6-(3-fluorobenzylamino)-2,4′-bipyridin-2′-yl-amino)cyclopentanecarboxylic acid U-31332-EXP080 (10 mg, 0.023 mmol), 2M dimethyl amine in THF (0.011 ml, 0.023 mmol), N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (8.70 mg, 0.045 mmol), 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol (4.32 mg, 0.032 mmol) were added then dimethylformamide (1 ml) and diisopropyl ethylamine (0.016 ml, 0.091 mmol) were added, and the reaction mixture was stirred at ambient temperature for 18 hr and the progress followed by LCMS. The crude reaction mixture was filtered and purified by preparative LC. The product fractions were combined, 50 mL of 1M NaOH and 50 mL of ethyl acetate were added. The organic layer was removed, washed with 50 mL 1M NaOH, 50 mL saturated salt solution, dried over sodium sulfate, and reduced to constant mass. 3 mg of the desired compound was obtained. LCMS (m/z): 468.1 (MH+), retention time=0.72 min., 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.77-2.16 (m, 6H) 2.96 (s, 3H) 3.07 (s, 3H) 3.10-3.25 (m, 1H) 4.29 (m, 1H) 4.56 (d, J=5.27 Hz, 2H) 5.12 (br. s., 1H) 5.87 (br. s., 1H) 6.38 (d, J=8.50 Hz, 1H) 6.58 (s, 1H) 6.91-7.01 (m, 1H) 7.06-7.20 (m, 1H) 7.26-7.37 (m, 2H) 7.44-7.53 (m, 1H) 8.09 (s, 1H).

Workup

  1. customThe crude reaction mixture
  2. filtrationwas filtered
  3. custompurified by preparative LC
  4. addition50 mL of 1M NaOH and 50 mL of ethyl acetate were added
  5. customThe organic layer was removed
  6. washwashed with 50 mL 1M NaOH, 50 mL saturated salt solution
  7. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-daa3c884cb8c4e5db52af386f6d63a6b
Source dataset
uspto-grants-2014_07
Patent number
US08778951B2

Reaction notes

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