N,N-Dimethylglycine → HCID 57584921, compound

HRID 2077584Notes

Reaction equation

HRID 2077584 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:17]=[CH:16][C:11]3[N:12]=[C:13]([NH2:15])[S:14][C:10]=3[CH:9]=2)=[CH:4][C:3]=1[N:18]([CH3:20])[CH3:19].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:45][N:46]([CH3:51])[CH2:47][C:48](O)=[O:49]>CN(C=O)C.O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:17]=[CH:16][C:11]3[N:12]=[C:13]([NH:15][C:48](=[O:49])[CH2:47][N:46]([CH3:51])[CH3:45])[S:14][C:10]=3[CH:9]=2)=[CH:4][C:3]=1[N:18]([CH3:20])[CH3:19]

Participants

6

Reactant 3

HCID 673N,N-DimethylglycineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57584985HCID 57584985, compound

Product 1

HCID 57584921HCID 57584921, compoundYield 33.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 6-(6-chloro-5-(dimethylamino)pyridin-3-yl)benzo[d]thiazol-2-amine (70 mg, 230 μmol), HATU (210 mg, 552 μmol), and 2-(dimethylamino)acetic acid (45 mg, 436 μmol) in DMF (2.5 mL) was heated to 60° C. for 2 h. The solution was diluted with H2O (20 mL) until it became cloudy and cooled to rt. The mixture was filtered, washed with H2O (10 mL), Na2HCO3 (saturated, 5 mL), and H2O (5 mL). The filter was dissolved in MeOH (10%) in DCM and dried over MgSO4. The organic was filtered, concentrated to a yellow solid. This was further purified on silica using MeOH in EtOAc (0-5%) to give a light yellow solid. A second purification with 1:1 hexane-acetone removed the less polar impurity (NAc) effectively, affording a white solid (30 mg). MS (ESI, POS. ION) M/Z: calc'd for C18H20ClN5OS: 389.1. found: 390.1. 1H NMR (400 MHz, chloroform-d) δ ppm 2.43 (s, 3H) 2.93 (s, 3H) 3.25 (s, 2H) 7.52 (d, J=2.15 Hz, 1H) 7.63 (dd, J=8.41, 1.76 Hz, 1H) 7.87 (d, J=8.41 Hz, 1H) 7.99 (d, J=1.56 Hz, 1H) 8.27 (d, J=2.15 Hz, 1H).

Workup

  1. temperaturecooled to rt
  2. filtrationThe mixture was filtered
  3. washwashed with H2O (10 mL), Na2HCO3 (saturated, 5 mL), and H2O (5 mL)
  4. dissolutionThe filter was dissolved in MeOH (10%) in DCM
  5. dry with materialdried over MgSO4
  6. filtrationThe organic was filtered
  7. concentrationconcentrated to a yellow solid
  8. customThis was further purified on silica
  9. customto give a light yellow solid
  10. customA second purification with 1:1 hexane-acetone
  11. customremoved the less polar impurity (NAc) effectively

Sources & evidence

ORD record
ord-d14c0c53cfe943cba27aac85516c4cac
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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