N,N-Dimethylglycine → HCID 178483960, compound

HRID 1623282Notes

Reaction equation

HRID 1623282 reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][C:4](O)=[O:5].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:41][C@H:42]1[CH2:47][CH2:46][C@H:45]([NH:48][C:49]2[CH:54]=[C:53]([C:55]3[CH:60]=[CH:59][CH:58]=[C:57]([NH:61][CH2:62][C:63]4[CH:68]=[CH:67][CH:66]=[C:65]([F:69])[CH:64]=4)[N:56]=3)[C:52]([Cl:70])=[CH:51][N:50]=2)[CH2:44][CH2:43]1>CS(C)=O.CN1C(=O)CCC1>[Cl:70][C:52]1[C:53]([C:55]2[CH:60]=[CH:59][CH:58]=[C:57]([NH:61][CH2:62][C:63]3[CH:68]=[CH:67][CH:66]=[C:65]([F:69])[CH:64]=3)[N:56]=2)=[CH:54][C:49]([NH:48][C@H:45]2[CH2:44][CH2:43][C@H:42]([NH:41][C:4](=[O:5])[CH2:3][N:2]([CH3:7])[CH3:1])[CH2:47][CH2:46]2)=[N:50][CH:51]=1

Participants

7

Reactant 4

HCID 673N,N-DimethylglycineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178511589HCID 178511589, compound

Product 1

HCID 178483960HCID 178483960, compoundYield 45.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 2-(dimethylamino)acetic acid (6.05 mg, 0.059 mmol), NMP (0.5 ml), Huenig's Base (0.023 ml, 0.132 mmol), and HATU (24.55 mg, 0.065 mmol) was stirred at ambient temperature for 5 minutes, followed by addition of N2′-(trans-4-aminocyclohexyl)-5′-chloro-N6-(3-fluorobenzyl)-2,4′-bipyridine-2′,6-diamine (Example 1) (12.5 mg, 0.029 mmol). The resulting mixture was stirred at ambient temperature for 4 hours. The crude reaction mixture was diluted with 0.25 ml of DMSO, filtered, purified by prep LC and then lyapholized to yield 6.8 mg of the title compound, as a TFA salt. LCMS (m/z): 511.3 (MH+), retention time=0.62 min.; 1H NMR (300 MHz, METHANOL-d4, 25° C.) δ ppm 1.32-1.53 (m, 4H) 1.98-2.07 (m, 2H) 2.07-2.18 (m, 2H) 2.92 (s, 6H) 3.60-3.68 (m, 1H) 3.70-3.82 (m, 1H) 3.90 (s, 2H) 4.63 (s, 2H) 6.83 (d, J=8.79 Hz, 1H) 6.86 (s, 1H) 6.93 (d, J=7.03 Hz, 1H) 6.99 (s, 1H) 7.10 (d, J=9.67 Hz, 1H) 7.18 (d, J=7.62 Hz, 1H) 7.28-7.40 (m, 1H) 7.68-7.77 (m, 1H) 8.01 (s, 1H)

Workup

  1. stirringThe resulting mixture was stirred at ambient temperature for 4 hours
  2. customThe crude reaction mixture
  3. filtrationfiltered
  4. custompurified by prep LC

Sources & evidence

ORD record
ord-4d7a2e44ce514460bfa9f9695b49efab
Source dataset
uspto-grants-2014_07
Patent number
US08778951B2

Reaction notes

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