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

HRID 1846549Notes

Reaction equation

HRID 1846549 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]([O:25][CH3:26])[N:22]=[C:21]([O:27][C:28]2[CH:37]=[C:36]([CH3:38])[C:31]3[NH:32][C:33](=[O:35])[O:34][C:30]=3[CH:29]=2)[CH:20]=1.CCN(C(C)C)C(C)C.O>CN(C=O)C>[CH3:26][O:25][C:23]1[N:24]=[C:19]([N:14]2[CH2:13][CH2:12][C:5]3([O:4][C:3](=[O:17])[NH:2][C:7]4[N:8]=[CH:9][CH:10]=[CH:11][C:6]3=4)[CH2:16][CH2:15]2)[CH:20]=[C:21]([O:27][C:28]2[CH:37]=[C:36]([CH3:38])[C:31]3[NH:32][C:33](=[O:35])[O:34][C:30]=3[CH:29]=2)[N:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 66687106Spiro[piperidine-4,4'-pyrido[2,3-d][1,3]oxazin]-2'(1'H)-one hydrochlorideHCID 866639146-(6-chloro-2-methoxypyrimidin-4-yloxy)-4-methylbenzo[d]oxazol-2(3H)-one

Product 1

HCID 462447611-[2-methoxy-6-(4-methyl-2-oxo-2,3-dihydrobenzo[d]oxazol-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

58 mg (0.23 mmol) spiro[piperidin-4,4′-pyrido[2,3-d][1,3]oxazin]-2′(1′H)-one hydrochloride, 70 mg (0.20 mmol) 6-(6-chloro-2-methoxypyrimidin-4-yloxy)-4-methylbenzo[d]oxazol-2(3H)-one and 0.10 mL DIPEA (0.57 mmol) in 1.0 mL DMF were stirred for 3 h at 90° C. The reaction mixture was mixed with water, the precipitate w suction filtered, washed and dried. The residue was purified by preparative HPLC-MS. The fractions containing product were combined and freeze-dried.

Workup

  1. filtrationfiltered
  2. washwashed
  3. customdried
  4. customThe residue was purified by preparative HPLC-MS
  5. additionThe fractions containing product
  6. customfreeze-dried

Sources & evidence

ORD record
ord-654839573e0242b0be5bf57d0f8399fe
Source dataset
uspto-grants-2015_02
Patent number
US08952014B2

Reaction notes

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