Diisopropylethylamine → HCID 71270301, compound

HRID 1842760Notes

Reaction equation

HRID 1842760 reaction equation
[Cl:1][C:2]1[C:3]([C:21]2[CH:22]=[N:23][N:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=23)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[C:12](F)=[CH:11][C:10]=2[O:19][CH3:20])=[N:6][CH:7]=1.[CH3:30][NH:31][CH2:32][CH2:33][N:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1.CCN(C(C)C)C(C)C>CC(N(C)C)=O.CO>[Cl:1][C:2]1[C:3]([C:21]2[CH:22]=[N:23][N:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=23)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[C:12]([N:31]([CH3:30])[CH2:32][CH2:33][N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)=[CH:11][C:10]=2[O:19][CH3:20])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 14979282Methyl(2-(morpholin-4-yl)ethyl)amineHCID 712393485-chloro-N-(4-fluoro-2-methoxy-5-nitrophenyl)-4-pyrazolo[1,5-a]pyridin-3-ylpyrimidin-2-amine2×

Product 1

HCID 71270301HCID 71270301, compoundYield 106.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
140 °C

Procedure

5-Chloro-N-(4-fluoro-2-methoxy-5-nitrophenyl)-4-pyrazolo[1,5-a]pyridin-3-ylpyrimidin-2-amine (Intermediate 20, 311 mg, 0.75 mmol), N-methyl-2-morpholinoethanamine (130 mg, 0.90 mmol) and DIPEA (0.157 mL, 0.90 mmol) were dissolved in DMA (3 mL) and sealed into a microwave tube. The mixture was heated to 140° C. for 0.75 h in the microwave then cooled to r.t. The mixture was then diluted with CH3OH and purified by ion exchange chromatography, using an SCX column and eluting with 1:1 7N methanolic ammonia in CH2Cl2. Appropriate fractions were combined and concentrated in vacuo to give the title compound (429 mg, 106%) as an orange solid which was used without further purification; 1H NMR: 2.36 (4H, s), 2.54 (2H, m), 2.89 (3H, s), 3.34 (2H, m), 3.49 (4H, m), 3.91 (3H, s), 6.81 (1H, s), 7.15 (1H, m), 7.35 (1H, t), 8.16 (1H, s), 8.45 (2H, m), 8.76 (1H, s), 8.86 (1H, d), 8.96 (1H, s); m/z: ES+ MH+ 539.

Workup

  1. customsealed into a microwave tube
  2. temperaturethen cooled to r.t
  3. custompurified by ion exchange chromatography
  4. washeluting with 1:1 7N methanolic ammonia in CH2Cl2
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1e5c7a8da2254c7ea4e0567c73004674
Source dataset
uspto-grants-2015_02
Patent number
US08946235B2

Reaction notes

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