N,N-Dimethylglycine → HCID 67003696, compound

HRID 2362674Notes

Reaction equation

HRID 2362674 reaction equation
[Cl:1][C:2]1[C:3]([C:19]2[S:23][C:22]([C:24]3([O:28][CH2:29][O:30][CH3:31])[CH2:27][CH2:26][CH2:25]3)=[N:21][CH:20]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][C:12]=3[F:18])[NH:8][C:5]2=[N:6][CH:7]=1.[CH3:32][N:33]([CH3:38])[CH2:34][C:35](O)=[O:36].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C)C=O.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[Cl:1][C:2]1[C:3]([C:19]2[S:23][C:22]([C:24]3([O:28][CH2:29][O:30][CH3:31])[CH2:25][CH2:26][CH2:27]3)=[N:21][CH:20]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:17]=[CH:16][C:14]([NH:15][C:35](=[O:36])[CH2:34][N:33]([CH3:38])[CH3:32])=[CH:13][C:12]=3[F:18])[NH:8][C:5]2=[N:6][CH:7]=1

Participants

7

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)2×HCID 67003470HCID 67003470, compound

Product 1

HCID 67003696HCID 67003696, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalyst2×HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-(5-chloro-4-(2-(1-(methoxymethoxy)cyclobutyl)thiazol-5-yl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-3-fluoroaniline (Example 60B) (68 mg, 0.148 mmol) and dimethyl glycine (15.3 mg, 0.148 mmol) in N,N-dimethylformamide (0.5 mL) was treated with O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (67.6 mg, 0.178 mmol) and 4-(dimethylamino)pyridine (1.8 mg, 0.015 mmol). The reaction was stirred for 16 hours at ambient temperature. The reaction was treated with more O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (67.6 mg, 0.178 mmol) and 4-(dimethylamino)pyridine (18.1 mg, 0.148 mmol), and the reaction was stirred another 16 hours at ambient temperature. The reaction was diluted with ethyl acetate and washed with water, saturated sodium bicarbonate solution, and brine. The organic layer was dried with sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with a gradient of 1 to 5% methanol in dichloromethane, to give the title compound. MS ESI(+) m/z 544.1 [M+H]+.

Workup

  1. stirringthe reaction was stirred another 16 hours at ambient temperature
  2. washwashed with water, saturated sodium bicarbonate solution, and brine
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel
  7. washeluting with a gradient of 1 to 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-0c05c70d139d463d9a67c52954493cad
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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