Water → 1-(6-(4-methyl-2-oxo-2,3-dihydrobenzo[d]oxazol-6-yloxy)-2-(trifluoromethyl)pyrimidin-4-yl)-spiro[piperidin-4,4'-pyrido[2,3-d][1,3]oxazin]-2'(1'H)-one

HRID 1846578Notes

Reaction equation

HRID 1846578 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]([C:25]([F:28])([F:27])[F:26])[N:22]=[C:21]([O:29][C:30]2[CH:39]=[C:38]([CH3:40])[C:33]3[NH:34][C:35](=[O:37])[O:36][C:32]=3[CH:31]=2)[CH:20]=1.CCN(C(C)C)C(C)C.O>CN1C(=O)CCC1>[CH3:40][C:38]1[C:33]2[NH:34][C:35](=[O:37])[O:36][C:32]=2[CH:31]=[C:30]([O:29][C:21]2[N:22]=[C:23]([C:25]([F:27])([F:26])[F:28])[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:39]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 66687106Spiro[piperidine-4,4'-pyrido[2,3-d][1,3]oxazin]-2'(1'H)-one hydrochlorideHCID 86663928HCID 86663928, compound

Product 1

HCID 462439821-(6-(4-methyl-2-oxo-2,3-dihydrobenzo[d]oxazol-6-yloxy)-2-(trifluoromethyl)pyrimidin-4-yl)-spiro[piperidin-4,4'-pyrido[2,3-d][1,3]oxazin]-2'(1'H)-one

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

90 mg (0.35 mmol) spiro[piperidin-4,4′-pyrido[2,3-d][1,3]oxazin]-2′(1′H)-one hydrochloride, 125 mg (0.36 mmol) 6-(6-chloro-2-trifluoromethyl-pyrimidin-4-yloxy)-4-methyl-3H-benzoxazol-2-one and 0.20 mL (1.16 mmol) DIPEA in 2.0 mL NMP were stirred for 14 h at 60° C. After cooling the reaction mixture was mixed with water and stirred for 30 min. The precipitate formed was suction filtered and dried.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. customThe precipitate formed
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-cd3883df07424759b3a64dcfd6e126b7
Source dataset
uspto-grants-2015_02
Patent number
US08952014B2

Reaction notes

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