Sodium Hydroxide → HCID 178428851, compound

HRID 1846568Notes

Reaction equation

HRID 1846568 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:38]=[C:37]([CH3:39])[C:29]3[NH:30][C:31]([C:33]([F:36])([F:35])[F:34])=[N:32][C:28]=3[CH:27]=2)[CH:20]=1.CCN(C(C)C)C(C)C.[OH-].[Na+]>CN(C=O)C>[CH3:39][C:37]1[C:29]2[NH:30][C:31]([C:33]([F:34])([F:36])[F:35])=[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:38]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 66687106Spiro[piperidine-4,4'-pyrido[2,3-d][1,3]oxazin]-2'(1'H)-one hydrochlorideHCID 178428835HCID 178428835, compound

Product 1

HCID 178428851HCID 178428851, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

21 mg (0.08 mmol) spiro[piperidin-4,4′-pyrido[2,3-d][1,3]oxazin]-2′(1′H)-one hydrochloride, 22 mg (0.07 mmol) 5-(6-chloropyrimidin-4-yloxy)-7-methyl-2-(trifluoromethyl)-1H-benzo[d]-imidazole and 40 μL (0.24 mmol) DIPEA in 2.0 mL DMF were stirred at 50° C. over the weekend. The reaction mixture was purified by chromatography. The fractions containing product were combined and evaporated down i.vac. to leave the aqueous residue. This was neutralised with a 1M aqueous NaOH solution. The precipitate formed was suction filtered, washed and dried.

Workup

  1. customThe reaction mixture was purified by chromatography
  2. additionThe fractions containing product
  3. customevaporated down i.vac
  4. customto leave the aqueous residue
  5. customThe precipitate formed
  6. filtrationfiltered
  7. washwashed
  8. customdried

Sources & evidence

ORD record
ord-de75791a9547485a9a323cd185394149
Source dataset
uspto-grants-2015_02
Patent number
US08952014B2

Reaction notes

Loading…