Water → N-(3-{[6-chloro-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-2-yl]amino}-2,2-dimethylpropyl)acetamide

HRID 2089013Notes

Reaction equation

HRID 2089013 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]([CH3:14])([CH3:13])[CH2:11][NH2:12])[CH:5]=[C:4]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)[CH:3]=1.C(N([CH2:29][CH3:30])CC)C.C(Cl)CCCCCCCCCCCCCCC.[OH2:48]>CN(C=O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]([CH3:14])([CH3:13])[CH2:11][NH:12][C:29](=[O:48])[CH3:30])[CH:5]=[C:4]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 209931-ChlorohexadecaneHCID 49830295N-[6-chloro-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-2-yl]-2,2-dimethylpropane-1,3-diamine

Product 1

HCID 87191721N-(3-{[6-chloro-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-2-yl]amino}-2,2-dimethylpropyl)acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 74 (100.0 mg, 0.303 mmol), triethylamine (0.055 mL, 0.394 mmol), and cetyl chloride (0.024 mL, 0.334 mmol) in DMF (2.2 mL) was stirred at 0° C. for 60 minutes. Water was added slowly to the reaction mixture and a white suspension formed. The suspension was filtered, washed with water and diethyl ether, and oven-dried to give 45.0 mg of the title compound. 1H NMR (300 MHz, DMSO-d6) ppm 0.87 (s, 6H), 1.89 (s, 3H), 2.96 (d, J=6.44 Hz, 2H), 3.13 (d, J=6.10 Hz, 2H), 6.86 (t, J=6.27 Hz, 1H), 6.90 (d, J=1.36 Hz, 1H), 6.98 (s, 1H), 7.22 (dd, J=7.80, 4.75 Hz, 1H), 7.79 (t, J=6.27 Hz, 1H), 8.15 (d, J=2.37 Hz, 1H), 8.27-8.40 (m, 2H), 12.16 (s, 1H). MS (ESI+) m/z 372.0 (M+H)+.

Workup

  1. customa white suspension formed
  2. filtrationThe suspension was filtered
  3. washwashed with water and diethyl ether
  4. customoven-dried

Sources & evidence

ORD record
ord-f52c40c14f124e4c8bdc7b820d1c7cde
Source dataset
uspto-grants-2013_05
Patent number
US08435980B2

Reaction notes

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