Diisopropylethylamine → HCID 178510001, compound

HRID 1696263Notes

Reaction equation

HRID 1696263 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]2[C:13]([C:14]([NH2:16])=[O:15])=[CH:12][N:11]=[C:10]3[NH:17][CH:18]=[N:19][C:9]=23)[CH2:3][CH2:2]1.Cl[C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][N:22]=1.C(N(CC)C(C)C)(C)C>CN1C(=O)CCC1.CCOC(C)=O.C(=O)([O-])O.[Na+]>[C:25]([C:24]1[CH:27]=[CH:28][C:21]([N:1]2[CH2:6][CH2:5][CH:4]([NH:7][C:8]3[C:13]([C:14]([NH2:16])=[O:15])=[CH:12][N:11]=[C:10]4[NH:17][CH:18]=[N:19][C:9]=34)[CH2:3][CH2:2]2)=[N:22][CH:23]=1)#[N:26]

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 178513741HCID 178513741, compound

Product 1

HCID 178510001HCID 178510001, compoundYield 10.9%

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 7-(4-piperidinylamino)-3H-imidazo[4,5-b]pyridine-6-carboxamide (46 mg), 6-chloronicotinonitrile (37 mg) and N,N-diisopropylethylamine (46 uL) in NMP (0.5 mL) was heated in the microwave reactor (90° C., 10 minutes). The reaction mixture was allowed to cool to ambient temperature and diluted with EtOAc (20 mL) and half-saturated aqueous sodium hydrogencarbonate (20 mL). The aqueous phase was extracted with EtOAc (2×20 mL) and combined organic layers were washed with brine (20 mL), dried over MgSO4, and concentrated. Purification of the product by column chromatography (silica gel, gradient elution, chloroform:methanol=20:1 to 10:1) provided (7 mg) 7-{[1-(5-cyano-2-pyridinyl)-4-piperidinyl]amino}-3H-imidazo[4,5-b]pyridine-6-carboxamide as a white solid.

Workup

  1. temperatureto cool to ambient temperature
  2. extractionThe aqueous phase was extracted with EtOAc (2×20 mL)
  3. washwere washed with brine (20 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customPurification of the product
  7. washby column chromatography (silica gel, gradient elution, chloroform:methanol=20:1 to 10:1)

Sources & evidence

ORD record
ord-88e62337dd4745098f7fbba42685a005
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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