Diisopropylethylamine → HCID 178428850, compound

HRID 1846570Notes

Reaction equation

HRID 1846570 reaction equation
Cl.[NH:2]1[C:7]2[N:8]=[CH:9][CH:10]=[CH:11][C:6]=2[C:5]2([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[O:4][C:3]1=[O:17].[CH3:18][C:19]1[C:24]2[NH:25][C:26]([CH:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[N:27][C:23]=2[CH:22]=[C:21]([O:34][C:35]2[CH:40]=[C:39](Cl)[N:38]=[CH:37][N:36]=2)[CH:20]=1.CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH3:18][C:19]1[C:24]2[NH:25][C:26]([CH:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[N:27][C:23]=2[CH:22]=[C:21]([O:34][C:35]2[N:36]=[CH:37][N:38]=[C:39]([N:14]3[CH2:13][CH2:12][C:5]4([O:4][C:3](=[O:17])[NH:2][C:7]5[N:8]=[CH:9][CH:10]=[CH:11][C:6]4=5)[CH2:16][CH2:15]3)[CH:40]=2)[CH:20]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 66687106Spiro[piperidine-4,4'-pyrido[2,3-d][1,3]oxazin]-2'(1'H)-one hydrochlorideHCID 178428834HCID 178428834, compound

Product 1

HCID 178428850HCID 178428850, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

33 mg (0.13 mmol) spiro[piperidin-4,4′-pyrido[2,3-d][1,3]oxazin]-2′(1′H)-one hydrochloride, 40 mg (0.12 mmol) 7-methyl-5-(6-chloropyrimidin-4-yloxy)-2-(tetrahydro-2H-pyran-4-yl)-1H-benzo[d]imidazole and 70 μL (0.39 mmol) DIPEA in 2.0 mL DMF were stirred overnight at 60° C. The reaction mixture was poured onto ice water and the precipitate formed was suction filtered. The precipitate was dissolved and then purified by chromatography. The fractions containing product were combined and evaporated down i.vac. to leave the aqueous residue. This was neutralised with an aqueous NaHCO3 solution. The precipitate formed was suction filtered, washed and dried.

Workup

  1. additionThe reaction mixture was poured onto ice water
  2. customthe precipitate formed
  3. filtrationfiltered
  4. dissolutionThe precipitate was dissolved
  5. custompurified by chromatography
  6. additionThe fractions containing product
  7. customevaporated down i.vac
  8. customto leave the aqueous residue
  9. customThe precipitate formed
  10. filtrationfiltered
  11. washwashed
  12. customdried

Sources & evidence

ORD record
ord-f27b6c04b68443ec8b6258f5457beee9
Source dataset
uspto-grants-2015_02
Patent number
US08952014B2

Reaction notes

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