Dimethylamine → HCID 178466732, compound

HRID 511035Notes

Reaction equation

HRID 511035 reaction equation
[Cl:1][C:2]1[C:3]([F:32])=[C:4]([C:23]2[CH:24]=[CH:25][C:26]([C:29]([OH:31])=O)=[N:27][CH:28]=2)[C:5]([O:20][CH2:21][CH3:22])=[C:6]([CH:8]([NH:10][C:11]2[N:19]=[CH:18][N:17]=[C:16]3[C:12]=2[N:13]=[CH:14][NH:15]3)[CH3:9])[CH:7]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)[N:51]([CH3:53])[CH3:52])C2C=CC=CC=2N=N1.CNC.C1COCC1.C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[C:3]([F:32])=[C:4]([C:23]2[CH:24]=[CH:25][C:26]([C:29]([N:51]([CH3:53])[CH3:52])=[O:31])=[N:27][CH:28]=2)[C:5]([O:20][CH2:21][CH3:22])=[C:6]([CH:8]([NH:10][C:11]2[N:19]=[CH:18][N:17]=[C:16]3[C:12]=2[N:13]=[CH:14][NH:15]3)[CH3:9])[CH:7]=1

Participants

8

Reactant 5

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 178466733HCID 178466733, compound

Product 1

HCID 178466732HCID 178466732, compoundYield 7.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 5-{3-chloro-6-ethoxy-2-fluoro-5-[1-(9H-purin-6-ylamino)ethyl]phenyl}pyridine-2-carboxylic acid (61 mg, 0.13 mmol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (0.11 g, 0.26 mmol) in DMF (1.4 mL) was treated with 2.0 M dimethylamine in THF (0.26 mL, 0.52 mmol) followed by triethylamine (0.072 mL, 0.52 mmol) and stirred at 20° C. for 3 hours. The reaction mixture was diluted with EtOAc and washed with water and brine. The organic layer was separated, dried with magnesium sulfate, filtered, and concentrated to give a crude oil. The crude material was purified by flash column chromatography using EtOAc in hexanes (0%-70%) to give the desired product (4.7 mg, 7%). LCMS for C23H24ClFN7O2 (M+H)+: m/z=484.2. Found: 484.1.

Workup

  1. washwashed with water and brine
  2. customThe organic layer was separated
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude oil
  7. customThe crude material was purified by flash column chromatography

Sources & evidence

ORD record
ord-77d7070ca99a49f8a3a492ca06fa9eea
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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