Diisopropylethylamine → HCID 86608559, compound

HRID 2243686Notes

Reaction equation

HRID 2243686 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].C[N:41]([CH:49]1CCNC[CH2:50]1)[C:42](=[O:48])[O:43][C:44]([CH3:47])([CH3:46])[CH3:45].C([N:58]([CH2:62][CH3:63])[CH:59]([CH3:61])C)(C)C>C1COCC1.CN(C=O)C>[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]([N:58]3[CH2:59][CH2:61][CH:50]([CH2:49][NH:41][C:42](=[O:48])[O:43][C:44]([CH3:47])([CH3:46])[CH3:45])[CH2:63][CH2:62]3)[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([C:22]([NH:24][C:25]4[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=4)=[O:23])[CH:32]=[CH:33][C:34]=3[CH3:35])[C:13]=2[CH2:12][NH:11][C:10]1=[O:39]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 27568064-N-Boc-4-N-Methyl-aminopiperidineHCID 119500953-[8-(2,6-difluorophenyl)-2-(methylsulfinyl)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-N-(4-fluorophenyl)-4-methylbenzamide

Product 1

HCID 86608559HCID 86608559, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 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 (40 mg, 0.073 mmol) in THF (3 mL) and DMF (0.5 mL) were added 1,1-dimethylethyl methyl(4-piperidinyl)carbamate (49 mg, 0.229 mmol) and N,N-diisopropylethylamine (0.1 mL, 0.574 mmol). The resultant solution was stirred at room temperature over night. The result mixture was concentrated. Flash chromatography (mobile phase DCM/DCM [90]+MeOH[7]+NH4OH[3]) provided the title compound as a white solid (12 mg, 25%). LC-MS m/z 702 (M+H)+.

Workup

  1. concentrationThe result mixture was concentrated

Sources & evidence

ORD record
ord-0284438e8b0944809f4a8946b9f4a612
Source dataset
uspto-grants-2010_03
Patent number
US07674789B2

Reaction notes

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