Diisopropylethylamine → HCID 67278084, compound

HRID 1696222Notes

Reaction equation

HRID 1696222 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]2[NH:13][CH:14]=[CH:15][C:3]=12.Cl.[CH3:17][C@@H:18]1[CH2:23][CH2:22][CH2:21][CH2:20][C@@H:19]1[NH2:24].[CH:25](N(CC)C(C)C)(C)C>C(O)CCC>[CH3:25][N:24]([C@H:19]1[CH2:20][CH2:21][CH2:22][CH2:23][C@H:18]1[CH3:17])[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]2[NH:13][CH:14]=[CH:15][C:3]=12

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 53438275Ethyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylateHCID 67278079(1S,2R)-2-methylcyclohexanamine hydrochloride

Product 1

HCID 67278084HCID 67278084, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

In a microwave reaction vessel ethyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (15 mg) and (1S,2R)-2-methylcyclohexanamine hydrochloride (65.5 mg) were suspended in n-butanol (0.075 mL). To the mixture was added N,N-diisopropylethylamine (0.093 mL). The vessel was sealed and reacted in the microwave reactor at 160° C. for 1 hour. The mixture was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel with chloroform and methanol (100:0 to 90:10) to give ethyl 4-{methyl[(1S,2R)-2-methylcyclohexyl]amino}-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (5 mg) as a white powder.

Workup

  1. customThe vessel was sealed
  2. customreacted in the microwave reactor at 160° C. for 1 hour
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customthe residue was purified by column chromatography on silica gel with chloroform and methanol (100:0 to 90:10)

Sources & evidence

ORD record
ord-c3ff7c605b0c4d08b10a8e502c46df25
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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