1-Methyl-1H-pyrrole-2-carbonyl chloride → N-[3-[3-[2-(2,3-dihydro-1,4-benzodioxin-6-ylamino)pyrimidin-4-yl]pyrazolo[1,5-a]pyridin-2-yl]phenyl]-1-methylpyrrole-2-carboxamide

HRID 1159878Notes

Reaction equation

HRID 1159878 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:24]4[CH:33]=[CH:32][C:27]5[O:28][CH2:29][CH2:30][O:31][C:26]=5[CH:25]=4)[N:18]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:34][N:35]1[CH:39]=[CH:38][CH:37]=[C:36]1[C:40](Cl)=[O:41]>C1COCC1.C(Cl)Cl>[O:28]1[C:27]2[CH:32]=[CH:33][C:24]([NH:23][C:19]3[N:18]=[C:17]([C:16]4[C:8]([C:4]5[CH:3]=[C:2]([NH:1][C:40]([C:36]6[N:35]([CH3:34])[CH:39]=[CH:38][CH:37]=6)=[O:41])[CH:7]=[CH:6][CH:5]=5)=[N:9][N:10]5[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=45)[CH:22]=[CH:21][N:20]=3)=[CH:25][C:26]=2[O:31][CH2:30][CH2:29]1

Participants

5

Reactant 2

HCID 27950921-Methyl-1H-pyrrole-2-carbonyl chlorideHCID 595138174-[2-(3-Aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-pyrimidinamine

Product 1

HCID 44529094N-[3-[3-[2-(2,3-dihydro-1,4-benzodioxin-6-ylamino)pyrimidin-4-yl]pyrazolo[1,5-a]pyridin-2-yl]phenyl]-1-methylpyrrole-2-carboxamideYield 92%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {4-[2-(3-amino-phenyl)-pyrazolo[1,5-a]pyridin-3-yl]-pyrimidin-2-yl}-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-amine (105 mg, 0.24 mmol) in 5 mL THF was added N-methylpyrrole carbonyl chloride (37 mg, 0.26 mmol). When TLC showed the reaction to be complete, the solution was diluted with DCM and washed with a solution of saturated NaHCO3 and with brine. The organic phase was dried over MgSO4 and concentrated. The residue was triturated with diethyl ether to give the title compound as a yellow solid (119 mg, 92%). 1H NMR (400 MHz, d6-DMSO) δ 9.90 (s, 1H), 9.80 (s, 1H), 8.87 (d, J=6.8 Hz, 1H), 8.50 (s, 1H), 8.14 (d, J=6.0 Hz, 1H), 8.05 (s, 1H), 7.88 (d, J=8.0 Hz, 1H), 7.51 (m, 1H), 7.43 (m, 1H), 7.27-7.22 (m, 2H), 7.17 (t, J=6.8 Hz, 1H), 7.05-7.04 (m, 2H), 7.00 (s, 1H), 6.81 (d, J=8.4 Hz, 1H), 6.47 (d, J=6.0 Hz, 1H), 6.08-6.07 (m, 1H), 4.22 (m, 4H), 3.85 (s, 3H) ppm. HRMS calculated C31H25N7O3 [M+H]+ 544.2097 found 544.2101.

Workup

  1. customthe reaction
  2. washwashed with a solution of saturated NaHCO3 and with brine
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-6f5f2d5f250b44f8aca7a80ce649249a
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

Loading…