Tetrahydrofuran → HCID 57737254, compound

HRID 1157645Notes

Reaction equation

HRID 1157645 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:18]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([NH:25][C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH2:33][CH2:34][N:35]([CH3:37])[CH3:36])[CH:27]=4)[N:20]=3)=[C:11]3[CH:12]=[CH:13][C:14]([O:16][CH3:17])=[CH:15][N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[C:38]1(/[CH:44]=[CH:45]/[CH2:46]Cl)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.C1C[O:51][CH2:50]C1>C(Cl)Cl>[CH3:37][N:35]([CH3:36])[CH2:34][CH2:33][O:32][C:28]1[CH:27]=[C:26]([NH:25][C:21]2[N:20]=[C:19]([C:18]3[C:8]([C:4]4[CH:3]=[C:2]([NH:1][C:50]([C:44]5([C:38]6[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=6)[CH2:46][CH2:45]5)=[O:51])[CH:7]=[CH:6][CH:5]=4)=[N:9][N:10]4[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=34)[CH:24]=[CH:23][N:22]=2)[CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 639658Cinnamyl chlorideHCID 57737217HCID 57737217, compound

Product 1

HCID 57737254HCID 57737254, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[2-(3-Aminophenyl)-6-(methyloxy)pyrazolo[1,5-a]pyridin-3-yl]-N-(3-{[2-(dimethylamino)ethyl]oxy}phenyl)-2-pyrimidinamine (97 mg, 0.20 mmol) and (2E)-3-phenyl-2-propenyl chloride (40 mg, 0.24 mmol) were combined in THF (2 mL) and stirred for 1 h. The mixture was diluted with DCM and TEA (2 drops), absorbed onto silica gel, and purified by silica gel chromatography to afford the title compound as a yellow solid (56 mg, 45%). 1H NMR (400 MHz, DMSO-d6) δ 10.34 (s, 1H), 9.55 (s, 1H), 8.57 (d, J=2.0 Hz, 1H), 8.45 (d, J=9.3 Hz, 1H), 8.23 (d, J=5.6 Hz, 1H), 7.97 (br s, 1H), 7.82 (d, J=7.9 Hz, 1H), 7.62-7.59 (m, 3H), 7.55-7.53 (m, 1H), 7.47-7.39 (m, 4H), 7.30-7.26 (m, 3H), 7.14 (m, 1H), 6.81 (d, J=15.6 Hz, 1H), 6.52 (dd, J=8.2, 2.5 Hz, 1H), 6.48 (d, J=5.3 Hz, 1H), 3.99 (t, J=6.0 Hz, 3H), 3.87 (s, 3H), 2.68-2.64 (m, 2H), 2.23 (s, 6H). ES-LC/MS m/z=626 [M+H]+.

Workup

  1. customabsorbed onto silica gel
  2. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-8ff2cf04511640299241d525264a6d11
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

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