Diisopropylethylamine → HCID 25265436, compound

HRID 2096372Notes

Reaction equation

HRID 2096372 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]=[C:23]([CH3:25])[N:22]=[C:21]([C:26]([C:28]2[CH:38]=[C:37]([CH3:39])[C:31]3[N:32]([CH3:36])[C:33](=[O:35])[O:34][C:30]=3[CH:29]=2)=[O:27])[CH:20]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:36][N:32]1[C:31]2[C:37]([CH3:39])=[CH:38][C:28]([C:26]([C:21]3[N:22]=[C:23]([CH3:25])[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)=[O:27])=[CH:29][C:30]=2[O:34][C:33]1=[O:35]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 581811376-(6-chloro-2-methyl-pyrimidine-4-carbonyl)-3,4-dimethyl-3H-benzoxazol-2-oneHCID 66687106Spiro[piperidine-4,4'-pyrido[2,3-d][1,3]oxazin]-2'(1'H)-one hydrochloride

Product 1

HCID 25265436HCID 25265436, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

77 mg (0.30 mmol) spiro[piperidin-4,4′-pyrido[2,3-d][1,3]oxazin]-2′(1′H)-one hydrochloride, 88 mg (0.28 mmol) 6-(6-chloro-2-methyl-pyrimidin-4-carbonyl)-3,4-dimethyl-3H-benzoxazol-2-one and 0.17 mL (1.0 mmol) DIPEA were combined in 2 mL DMF and stirred overnight at RT. Then the reaction mixture was purified by preparative HPLC-MS. The fractions containing the product were combined and the organic solvent was evaporated down. The residue was neutralised with 4N aqueous sodium hydroxide solution. The precipitate formed was suction filtered, washed with water and dried i. vac.

Workup

  1. customThen the reaction mixture was purified by preparative HPLC-MS
  2. additionThe fractions containing the product
  3. customthe organic solvent was evaporated down
  4. customThe precipitate formed
  5. filtrationfiltered
  6. washwashed with water
  7. customdried i

Sources & evidence

ORD record
ord-3f57570a76df427ca09b2618bbef7ec1
Source dataset
uspto-grants-2013_05
Patent number
US08450327B2

Reaction notes

Loading…