Propyl isocyanate → (2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)-N-propylpiperidine-1-carboxamide

HRID 74880

Reaction equation

HRID 74880 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15]([NH:17]C4CCCNC4)[C:14]([F:24])=[CH:13][N:12]=3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.ClC1C=C2C(C3N=C(N[C@H:42]4[CH2:47][CH2:46][CH2:45][NH:44][CH2:43]4)C(F)=CN=3)=CNC2=NC=1.[CH2:49]([N:52]=[C:53]=[O:54])[CH2:50][CH3:51]>C(Cl)Cl.N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15]([NH:17][CH:43]4[CH2:42][CH2:47][CH2:46][CH2:45][N:44]4[C:53]([NH:52][CH2:49][CH2:50][CH3:51])=[O:54])[C:14]([F:24])=[CH:13][N:12]=3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 61033Propyl isocyanateHCID 575977382-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoro-N-(piperidin-3-yl)pyrimidin-4-amineHCID 67287752(S)-2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoro-N-(piperidin-3-yl)pyrimidin-4-amine

Product 1

HCID 86762723(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)-N-propylpiperidine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 21875418Pyridine methylene chlorideSolvent

Procedure

To a solution of 2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoro-N-(piperidin-3-yl)pyrimidin-4-amine, 5b, (0.020 g, 0.058 mmol) in 1:1 mixture of CH2Cl2/pyridine (2 mL) was added propylisocyanate (0.005 mL, 0.058 mmol). The reaction mixture was stirred at room temperature for 12 hours. The resulting residue was purified by preparatory HPLC (0.1% TFA-H2O/acetonitrile) to afford the desired product, 196.

Workup

  1. customThe resulting residue was purified by preparatory HPLC (0.1% TFA-H2O/acetonitrile)

Sources & evidence

ORD record
ord-147cd01489ba4e18a1d4b41c0d4de8fc
Source dataset
uspto-grants-2014_09
Patent number
US08829007B2

Linked notes

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