2,2-Dimethyl-1,3-propanediamine → N-[6-chloro-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-2-yl]-2,2-dimethylpropane-1,3-diamine

HRID 2089003Notes

Reaction equation

HRID 2089003 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[NH:10][CH:9]=2)[CH:5]=[C:4]([Cl:17])[N:3]=1.[CH3:18][C:19]([CH3:24])([CH2:22][NH2:23])[CH2:20][NH2:21]>[Cl-].[Na+].O>[Cl:17][C:4]1[N:3]=[C:2]([NH:21][CH2:20][C:19]([CH3:24])([CH3:18])[CH2:22][NH2:23])[CH:7]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[NH:10][CH:9]=2)[CH:5]=1

Participants

4

Reactant 2

HCID 817702,2-Dimethyl-1,3-propanediamineHCID 87191335CID 87191335

Product 1

HCID 49830295N-[6-chloro-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-2-yl]-2,2-dimethylpropane-1,3-diamine

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of Example 61a (1.70 g, 6.44 mmol) and 2,2-dimethylpropane-1,3-diamine (10 mL) was heated in a Biotage microwave reactor at 160° C. for 25 minutes. The solution was diluted with 20% brine and washed with EtOAc (2×). The combined organic layers were washed with 20% brine, dried (MgSO4), filtered, and concentrated. The residue was triturated with EtOAc and diethyl ether. The solids were filtered, washed with ether, and dried to give 1.19 g of the title compound. 1H NMR (300 MHz, DMSO-d6) ppm 0.87 (s, 6H), 2.36 (s, 2H), 3.16 (d, J=6.10 Hz, 2H), 6.78-6.89 (m, 2H), 6.97 (d, J=1.02 Hz, 1H), 7.21 (dd, J=7.97, 4.58 Hz, 1H), 8.13 (s, 1H), 8.27-8.38 (m, 2H). MS (ESI+) m/z 329.9 (M+H)+.

Workup

  1. washwashed with EtOAc (2×)
  2. washThe combined organic layers were washed with 20% brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was triturated with EtOAc and diethyl ether
  7. filtrationThe solids were filtered
  8. washwashed with ether
  9. customdried

Sources & evidence

ORD record
ord-48d5e4f7a0b743319adc57f03b35698c
Source dataset
uspto-grants-2013_05
Patent number
US08435980B2

Reaction notes

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