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Diisopropylethylamine → 1-(6-(2,4-dimethyl-1H-benzo[d]imidazol-6-yloxy)pyrimidin-4-yl)spiro[piperidine-4,4'-pyrido-[2,3-d][1,3]oxazin]-2'(1'H)-one

HRID 1846540
Notes
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Reaction equation

HRID 1846540 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]([CH3:36])[C:29]3[N:33]=[C:32]([CH3:34])[NH:31][C:30]=3[CH:35]=2)[CH:20]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:34][C:32]1[NH:31][C:30]2[CH:35]=[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]([CH3:36])[C:29]=2[N:33]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 66687106Spiro[piperidine-4,4'-pyrido[2,3-d][1,3]oxazin]-2'(1'H)-one hydrochlorideHCID 866639086-(6-chloro-pyrimidin-4-yloxy)-2,4-dimethyl-1H-benzimidazole

Product 1

HCID 462445971-(6-(2,4-dimethyl-1H-benzo[d]imidazol-6-yloxy)pyrimidin-4-yl)spiro[piperidine-4,4'-pyrido-[2,3-d][1,3]oxazin]-2'(1'H)-one

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

0.15 g (0.59 mmol) spiro[piperidine-4,4′-pyrido[2,3-d][1,3]oxazin]-2′(1′H)-one hydrochloride, 0.15 g (0.55 mmol) 6-(6-chloro-pyrimidin-4-yloxy)-2,4-dimethyl-1H-benzimidazole and 0.31 mL (1.8 mmol) DIPEA were combined in 1.5 mL DMF and stirred first of all overnight at RT then for 2 h at 50° C. The reaction mixture was purified by preparative HPLC-MS. The product-containing fractions were combined and the acetonitrile was evaporated down. The residue was made alkaline with 4N aqueous sodium hydroxide solution, the precipitate formed was suction filtered, washed with water and dried under HV.

Workup

  1. waitfor 2 h at 50° C
  2. customThe reaction mixture was purified by preparative HPLC-MS
  3. customthe acetonitrile was evaporated down
  4. customthe precipitate formed
  5. filtrationfiltered
  6. washwashed with water
  7. customdried under HV

Sources & evidence

ORD record
ord-1e631c0d183a4802aa7816e7ffa94c3c
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08952014B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes