Diisopropylethylamine → HCID 68007463, compound

HRID 74896Notes

Reaction equation

HRID 74896 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15]([NH:17][CH2:18][CH:19]4[CH2:24][CH2:23][CH2:22][NH:21][CH2:20]4)[C:14]([F:25])=[CH:13][N:12]=3)=[CH:9][N:8](S(C3C=CC(C)=CC=3)(=O)=O)[C:5]2=[N:6][CH:7]=1.CCN(C(C)C)C(C)C.[CH3:45][O:46][CH2:47][CH2:48][C:49](Cl)=[O:50]>C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15]([NH:17][CH2:18][C@H:19]4[CH2:24][CH2:23][CH2:22][N:21]([C:49](=[O:50])[CH2:48][CH2:47][O:46][CH3:45])[CH2:20]4)[C:14]([F:25])=[CH:13][N:12]=3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27597283-Methoxypropanoyl chlorideHCID 672856162-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoro-N-(piperidin-3-ylmethyl)pyrimidin-4-amine2×

Product 1

HCID 68007463HCID 68007463, compound

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

To a solution of 2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoro-N-(piperidin-3-ylmethyl)pyrimidin-4-amine, 11c, (0.04 g, 0.11 mmol) in a 10:1 mixture of CH2Cl2/DMF (1 mL) was added iPr2NEt (0.058 mL, 0.33 mmol) and 3-methoxypropanoyl chloride (0.02 g, 0.17 mmol). After 12 hours, the solvent was concentrated in vacuo and the resulting crude was and the crude was purified by preparatory HPLC (0.1% TFA-H2O/acetonitrile) to afford the desired product, 327.

Workup

  1. concentrationthe solvent was concentrated in vacuo
  2. customthe crude was purified by preparatory HPLC (0.1% TFA-H2O/acetonitrile)

Sources & evidence

ORD record
ord-b4af35c4d5954bfb9c75c4c5f5dcaa58
Source dataset
uspto-grants-2014_09
Patent number
US08829007B2

Reaction notes

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