N,N-Dimethylglycine → HCID 67003675, compound

HRID 2362649Notes

Reaction equation

HRID 2362649 reaction equation
[Cl:1][C:2]1[C:3]([C:18]2[S:22][C:21]([C:23]3([O:27][CH2:28][O:29][CH3:30])[CH2:26][CH2:25][CH2:24]3)=[N:20][CH:19]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=3)[NH:8][C:5]2=[N:6][CH:7]=1.[CH3:31][N:32]([CH3:37])[CH2:33][C:34](O)=[O:35].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=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:18]2[S:22][C:21]([C:23]3([O:27][CH2:28][O:29][CH3:30])[CH2:24][CH2:25][CH2:26]3)=[N:20][CH:19]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([NH:15][C:34](=[O:35])[CH2:33][N:32]([CH3:37])[CH3:31])=[CH:16][CH:17]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

8

Reactant 4

HCID 673N,N-DimethylglycineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 67003496HCID 67003496, compound

Product 1

HCID 67003675HCID 67003675, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 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)aniline (Example 23B) (20 mg, 0.045 mmol) and dimethyl glycine (5.61 mg, 0.054 mmol) in N,N-dimethylformamide (0.5 mL) was treated with N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (10.43 mg, 0.054 mmol), and 1-hydroxybenzotriazole hydrate (8.34 mg, 0.054 mmol). The reaction was stirred for 4 hours at ambient temperature. The reaction was treated with 4-(dimethylamino)pyridine (5.50 mg, 0.045 mmol), and the reaction was stirred 4 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 2 to 10% methanol in dichloromethane, to give the title compound. MS ESI(+) m/z 526.0 [M+H]+.

Workup

  1. stirringthe reaction was stirred 4 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 2 to 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-8476c3f949d340ce9b199e7d253be87c
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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