N,N-Dimethylglycine → HCID 86691103, compound

HRID 1406322Notes

Reaction equation

HRID 1406322 reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][C:4](O)=[O:5].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[F:39][C:40]1[CH:41]=[CH:42][C:43]([N:67]2[N:71]=[CH:70][CH:69]=[N:68]2)=[C:44]([C@H:46]([O:48][C:49]2[C:50]([NH2:66])=[N:51][CH:52]=[C:53]([C:55]3[CH:56]=[N:57][N:58]([CH:60]4[CH2:65][CH2:64][NH:63][CH2:62][CH2:61]4)[CH:59]=3)[CH:54]=2)[CH3:47])[CH:45]=1>CS(C)=O.CO>[NH2:66][C:50]1[N:51]=[CH:52][C:53]([C:55]2[CH:56]=[N:57][N:58]([CH:60]3[CH2:61][CH2:62][N:63]([C:4](=[O:5])[CH2:3][N:2]([CH3:7])[CH3:1])[CH2:64][CH2:65]3)[CH:59]=2)=[CH:54][C:49]=1[O:48][C@@H:46]([C:44]1[CH:45]=[C:40]([F:39])[CH:41]=[CH:42][C:43]=1[N:67]1[N:71]=[CH:70][CH:69]=[N:68]1)[CH3:47]

Participants

7

Reactant 4

HCID 673N,N-Dimethylglycine2×HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2×HCID 67463510HCID 67463510, compound

Product 1

HCID 86691103HCID 86691103, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

To a solution of 2-(dimethylamino)acetic acid (54 mg, 0.55 mmol) and HATU (105 mg, 0.27 mmol) in DMSO (1 mL) was added triethylamine (0.063 ml, 0.46 mmol). After stirring for ˜15 min, the mixture was added to a flask containing 3-{(1R)-1-[5-fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl]ethoxy}-5-[1-(piperidin-4-yl)-1H-pyrazol-4-yl]pyridin-2-amine (example 80) (43 mg, 0.09 mmol. The mixture was stirred at room temperature for 18 hr. Additional portion of 2-(dimethylamino)acetic acid (28 mg), HATU (105 mg) and TEA (63 μL) were added and the mixture was stirred at RT for 2 hr. LCMS indicated the reaction complete. The mixture was diluted with MeOH and purified by reverse phase prep-HPLC. The desired fractions were lyophilized to give the title compound as an acetic acid salt (17 mg).

Workup

  1. additionthe mixture was added to a flask
  2. stirringThe mixture was stirred at room temperature for 18 hr
  3. stirringthe mixture was stirred at RT for 2 hr
  4. custompurified by reverse phase prep-HPLC

Sources & evidence

ORD record
ord-3ea49bc67b274cf895173c167e661188
Source dataset
uspto-grants-2014_12
Patent number
US08916593B2

Reaction notes

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