Triethylamine → HCID 86608561, compound

HRID 2243746Notes

Reaction equation

HRID 2243746 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)=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][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])[C:13]=2[CH2:12][NH:11][C:10]1=[O:40].C[N:42]([CH:50]1CCNC[CH2:51]1)[C:43](=[O:49])[O:44][C:45]([CH3:48])([CH3:47])[CH3:46].C([N:58]([CH2:61][CH3:62])[CH2:59][CH3:60])C>C(Cl)Cl.CCOC(C)=O>[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][CH2:60][CH:51]([CH2:50][NH:42][C:43](=[O:49])[O:44][C:45]([CH3:48])([CH3:47])[CH3:46])[CH2:62][CH2:61]3)[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([C:22]([NH:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[O:23])[CH:32]=[CH:33][C:34]=3[CH3:35])[C:13]=2[CH2:12][NH:11][C:10]1=[O:40]

Participants

6

Reactant 3

HCID 8471Triethylamine2×HCID 27568064-N-Boc-4-N-Methyl-aminopiperidine2×HCID 11950098HCID 11950098, compound

Product 1

HCID 86608561HCID 86608561, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Compound 3-[8-(2,6-difluorophenyl)-2-(methylsulfonyl)-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4-yl]-4-methyl-N-(phenylmethyl)benzamide (0.0811 g, 0.144 mmol) was dissolved in CH2Cl2 (5 mL) and 1,1-dimethylethyl methyl(4-piperidinyl)carbamate (0.0394 g, 0.18 mmol) and triethylamine (0.029 g, 0.288 mmol) were added. The reaction mixture was stirred for 4 days. Additional 1,1-dimethylethyl methyl(4-piperidinyl)carbamate (0.0788 g, 0.36 mmol) and triethylamine (0.058 g, 0.576 mmol) were added and the mixture was stirred under argon at room temperature for an additional 7 days. The solvents were pumped off in vacuo, and the residue taken up in EtOAc and washed with 1 N NaOH, brine, dried over anhydrous Na2SO4 filtered and evaporated. The residue was flash chromatographed on silica gel (20 g) eluted with 0-70% EtOAc/hexane. Some impurities remained, so the material was rechromatographed on silica gel (20 g) eluted with 0-50% EtOAc/hexane to give the title compound as a white amorphous solid. mp (dec) 146-150° C. LC-MS m/z 698 (M+H)+, 2.66 min (ret time).

Workup

  1. stirringthe mixture was stirred under argon at room temperature for an additional 7 days
  2. washwashed with 1 N NaOH, brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customchromatographed on silica gel (20 g)
  7. washeluted with 0-70% EtOAc/hexane
  8. customwas rechromatographed on silica gel (20 g)
  9. washeluted with 0-50% EtOAc/hexane

Sources & evidence

ORD record
ord-d7718cf953ea473191f9ff1e3ba7a8ac
Source dataset
uspto-grants-2010_03
Patent number
US07674789B2

Reaction notes

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