N,N-Dimethylglycine → HCID 59506965, compound

HRID 1800601Notes

Reaction equation

HRID 1800601 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[C:6]([O:11][C:12]1[CH:13]=[C:14]([NH:19][C:20](=[O:32])[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([C:30]#[N:31])([CH3:29])[CH3:28])[CH:22]=3)[CH:15]=[CH:16][C:17]=1[CH3:18])[N:5]=2.[CH3:33][N:34]([CH3:39])[CH2:35][C:36](O)=[O:37].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(=O)([O-])O.[Na+]>N1C=CC=CC=1>[C:30]([C:27]([C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][CH:24]=1)[C:20]([NH:19][C:14]1[CH:15]=[CH:16][C:17]([CH3:18])=[C:12]([O:11][C:6]2[N:5]=[C:4]3[S:3][C:2]([NH:1][C:36](=[O:37])[CH2:35][N:34]([CH3:39])[CH3:33])=[N:10][C:9]3=[CH:8][CH:7]=2)[CH:13]=1)=[O:32])([CH3:29])[CH3:28])#[N:31]

Participants

6

Reactant 4

HCID 673N,N-DimethylglycineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86646043HCID 86646043, compound

Product 1

HCID 59506965HCID 59506965, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of N-{3-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-4-methylphenyl}-3-(1-cyano-1-methylethyl)benzamide (153 mg, 0.344 mmol) produced in Example C12(iv), N,N-dimethylglycine (79.5 mmol, 0.771 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (321 mg, 0.843 mmol) and pyridine (3 mL) was stirred at 100° C. for 15 hr. To the reaction mixture was added aqueous sodium hydrogen carbonate solution (5 mL), and the mixture was extracted with ethyl acetate (5 mL×4). The organic layers were combined, and dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=50/50→0/100), and crystallized from diisopropyl ether/ethyl acetate to give the title compound (25.4 mg, 14%) as pale-orange crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (5 mL×4)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=50/50→0/100)
  5. customcrystallized from diisopropyl ether/ethyl acetate

Sources & evidence

ORD record
ord-887669738f0f47f18394112397d13c74
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

Loading…