Diisopropylethylamine → HCID 178428849, compound

HRID 1846565Notes

Reaction equation

HRID 1846565 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].Cl[C:19]1[N:24]=[CH:23][N:22]=[C:21]([O:25][C:26]2[CH:39]=[C:38]([CH3:40])[C:29]3[NH:30][C:31]([CH:33]4[CH2:37][CH2:36][O:35][CH2:34]4)=[N:32][C:28]=3[CH:27]=2)[CH:20]=1.CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH3:40][C:38]1[C:29]2[NH:30][C:31]([CH:33]3[CH2:37][CH2:36][O:35][CH2:34]3)=[N:32][C:28]=2[CH:27]=[C:26]([O:25][C:21]2[N:22]=[CH:23][N:24]=[C:19]([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:20]=2)[CH:39]=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 178428833HCID 178428833, compound

Product 1

HCID 178428849HCID 178428849, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

138 mg (0.54 mmol) spiro[piperidin-4,4′-pyrido[2,3-d][1,3]oxazin]-2′(1′H)-one hydrochloride, 180 mg (0.54 mmol) 5-(6-chloropyrimidin-4-yloxy)-7-methyl-2-(tetrahydrofuran-3-yl)-1H-benzo[d]imidazole and 280 μL (1.62 mmol) DIPEA in 5.0 mL DMF were stirred overnight at 60° C. The reaction mixture was combined with ice water. The precipitate formed was suction filtered and 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 and extracted with ethyl acetate. The organic phase was dried and evaporated down i.vac.

Workup

  1. customThe precipitate formed
  2. filtrationfiltered
  3. custompurified by chromatography
  4. additionThe fractions containing product
  5. customevaporated down i.vac
  6. customto leave the aqueous residue
  7. extractionextracted with ethyl acetate
  8. customThe organic phase was dried
  9. customevaporated down i.vac

Sources & evidence

ORD record
ord-38c0fbdd09544336a26533d33cbaf538
Source dataset
uspto-grants-2015_02
Patent number
US08952014B2

Reaction notes

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