Diisopropylethylamine → HCID 46245272, compound

HRID 1846574Notes

Reaction equation

HRID 1846574 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]([CH3:40])[C:29]3[N:33]=[C:32]([C@H:34]4[CH2:38][CH2:37][CH2:36][O:35]4)[NH:31][C:30]=3[CH:39]=2)[CH:20]=1.CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH3:40][C:28]1[C:29]2[N:33]=[C:32]([C@H:34]3[CH2:38][CH2:37][CH2:36][O:35]3)[NH:31][C:30]=2[CH:39]=[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:27]=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 86663936HCID 86663936, compound

Product 1

HCID 46245272HCID 46245272, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

166 mg (0.65 mmol) spiro[piperidin-4,4′-pyrido[2,3-d][1,3]oxazin]-2′(1′H)-one hydrochloride, 205 mg (0.62 mmol) (R)-6-(6-chloropyrimidin-4-yloxy)-4-methyl-2-(tetrahydrofuran-2-yl)-1H-benzo[d]imidazole and 320 μL (1.86 mmol) DIPEA in 5.0 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 an aqueous NaHCO3 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-3a2c8d8a571d4f00a955fb68617ea27c
Source dataset
uspto-grants-2015_02
Patent number
US08952014B2

Reaction notes

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