Sodium Hydroxide → HCID 46245197, compound

HRID 1846571Notes

Reaction equation

HRID 1846571 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:27]=[C:28]([CH3:39])[C:29]3[N:33]=[C:32]([CH2:34][CH2:35][O:36][CH3:37])[NH:31][C:30]=3[CH:38]=2)[CH:20]=1.CCN(C(C)C)C(C)C.[OH-].[Na+]>CN(C=O)C>[CH3:37][O:36][CH2:35][CH2:34][C:32]1[NH:31][C:30]2[CH:38]=[C:26]([O:25][C:21]3[N:22]=[CH:23][N:24]=[C:19]([N:14]4[CH2:13][CH2:12][C:5]5([O:4][C:3](=[O:17])[NH:2][C:7]6[N:8]=[CH:9][CH:10]=[CH:11][C:6]5=6)[CH2:16][CH2:15]4)[CH:20]=3)[CH:27]=[C:28]([CH3:39])[C:29]=2[N:33]=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 86663934HCID 86663934, compound

Product 1

HCID 46245197HCID 46245197, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

29 mg (0.11 mmol) spiro[piperidin-4,4′-pyrido[2,3-d][1,3]oxazin]-2′(1′H)-one hydrochloride, 29 mg (0.09 mmol) 6-(6-chloropyrimidin-4-yloxy)-2-(2-methoxyethyl)-4-methyl-1H-benzo-[d]imidazole and 50 μL (0.39 mmol) DIPEA in 2.0 mL DMF were stirred overnight at 50° C. 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-fbe32ae09f04453d9fd5f0f1f3121050
Source dataset
uspto-grants-2015_02
Patent number
US08952014B2

Reaction notes

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