Diisopropylethylamine → 1-{6-[2-(methoxymethyl)-4-methyl-1H-benzo[d]imidazol-6-yloxy]pyrimidin-4-yl}spiro-(piperidin-4,4'-pyrido[2,3-d][1,3]oxazin)-2'(1'H)-one

HRID 1846547Notes

Reaction equation

HRID 1846547 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]([CH3:38])[C:29]3[N:33]=[C:32]([CH2:34][O:35][CH3:36])[NH:31][C:30]=3[CH:37]=2)[CH:20]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:36][O:35][CH2:34][C:32]1[NH:31][C:30]2[CH:37]=[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]([CH3:38])[C:29]=2[N:33]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 66687106Spiro[piperidine-4,4'-pyrido[2,3-d][1,3]oxazin]-2'(1'H)-one hydrochlorideHCID 866639136-(6-chloropyrimidin-4-yloxy)-2-(methoxymethyl)-4-methyl-1H-benzo[d]imidazole

Product 1

HCID 462447591-{6-[2-(methoxymethyl)-4-methyl-1H-benzo[d]imidazol-6-yloxy]pyrimidin-4-yl}spiro-(piperidin-4,4'-pyrido[2,3-d][1,3]oxazin)-2'(1'H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

49 mg (0.19 mmol) spiro[piperidin-4,4′-pyrido[2,3-d][1,3]oxazin]-2′(1′H)-one hydrochloride, 50 mg (0.16 mmol) 6-(6-chloropyrimidin-4-yloxy)-2-(methoxymethyl)-4-methyl-1H-benzo-[d]imidazole and 0.10 mL (0.57 mmol) DIPEA in 2.0 mL DMF were stirred at 40° C. over the weekend. The reaction mixture was purified by preparative HPLC-MS. The fractions containing product were partially evaporated down i.vac. and neutralised with 4M sodium hydroxide solution. The precipitate formed was suction filtered, washed and dried.

Workup

  1. customThe reaction mixture was purified by preparative HPLC-MS
  2. additionThe fractions containing product
  3. customwere partially evaporated down i.vac
  4. customThe precipitate formed
  5. filtrationfiltered
  6. washwashed
  7. customdried

Sources & evidence

ORD record
ord-6103fdbcb5774a52b6d8af4880aa60d1
Source dataset
uspto-grants-2015_02
Patent number
US08952014B2

Reaction notes

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