Dimethylformamide → HCID 59208135, compound

HRID 2243697Notes

Reaction equation

HRID 2243697 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16](S(C)=O)[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([CH:32]=[CH:33][C:34]=3[CH3:35])[C:22]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[O:23])[C:13]=2[CH2:12][NH:11][C:10]1=[O:39].CN(C=O)C.Cl.Cl.[NH:47]1[CH:51]=[CH:50][N:49]=[C:48]1[CH2:52][NH2:53].C(N(CC)C(C)C)(C)C>C1COCC1.C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16]([NH:53][CH2:52][C:48]3[NH:47][CH:51]=[CH:50][N:49]=3)[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([CH:32]=[CH:33][C:34]=3[CH3:35])[C:22]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[O:23])[C:13]=2[CH2:12][NH:11][C:10]1=[O:39]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 119500953-[8-(2,6-difluorophenyl)-2-(methylsulfinyl)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-N-(4-fluorophenyl)-4-methylbenzamideHCID 124178631H-imidazol-2-ylmethanamine dihydrochloride

Product 1

HCID 59208135HCID 59208135, compoundYield 33.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 3-[8-(2,6-difluorophenyl)-2-(methylsulfinyl)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-N-(4-fluorophenyl)-4-methylbenzamide (20 mg, 0.036 mmol) in THF(3 mL)/DMF(3 mL)/DCM(3 mL) were added (1H-imidazol-2-ylmethyl)amine dihydrochloride (50 mg, 0.52 mmol) and N,N-diisopropylethylamine (0.1 mL, 0.574 mmol). The resultant solution was stirred at 40° C. over night. The result mixture was concentrated. CombiFlash chromatography (mobile phase DCM/DCM[90]+MeOH[7]+NH4OH[3]) provided the title compound as a white solid (7 mg, 33%). LC-MS m/z 585 (M+H)+; 1H-NMR (MeOD) δ 2.33 (s, 3H), 4.13 (s, 2H), 4.42 (s, 2H), 6.92 (m, 2H), 7.15 (m, 4H), 7.50 (m, 2H), 7.72 (m, 2H), 7.82 (s, 1H), 7.98 (d, 1H).

Workup

  1. concentrationThe result mixture was concentrated

Sources & evidence

ORD record
ord-8b72621080bd407da39e9678b335c7a2
Source dataset
uspto-grants-2010_03
Patent number
US07674789B2

Reaction notes

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