Dimethylformamide → 1-(6-(4-methyl-2-oxo-2,3-dihydrobenz-[d]oxazol-6-yloxy)pyrimidin-4-yl)spiro[piperidin-4,4'-pyrido[2,3-d][1.3]oxazin]-2'(1'H)-one

HRID 1846534Notes

Reaction equation

HRID 1846534 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].ClC1N=CN=C(N[C:26]2[CH:35]=[C:34]([CH3:36])[C:29]3[NH:30][C:31](=[O:33])[O:32][C:28]=3[CH:27]=2)C=1.[CH3:37][CH2:38][N:39](C(C)C)C(C)C.[CH3:46][N:47]([CH:49]=[O:50])C>>[CH3:36][C:34]1[C:29]2[NH:30][C:31](=[O:33])[O:32][C:28]=2[CH:27]=[C:26]([O:50][C:49]2[N:47]=[CH:46][N:39]=[C:38]([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:37]=2)[CH:35]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 66687106Spiro[piperidine-4,4'-pyrido[2,3-d][1,3]oxazin]-2'(1'H)-one hydrochlorideHCID 866638946-(6-chloro-pyrimidin-4-ylamino)-4-methyl-3H-benzoxazol-2-one

Product 1

HCID 462362521-(6-(4-methyl-2-oxo-2,3-dihydrobenz-[d]oxazol-6-yloxy)pyrimidin-4-yl)spiro[piperidin-4,4'-pyrido[2,3-d][1.3]oxazin]-2'(1'H)-one

Procedure

20 mg (0.078 mol) spiro[piperidin-4,4′-pyrido[2,3-d][1,3]oxazin]-2′(1′H)-one hydrochloride, 20 mg (0.072 mmol) 6-(6-chloro-pyrimidin-4-ylamino)-4-methyl-3H-benzoxazol-2-one and 0.10 mL (0.57 mmol) DIPEA were combined in 1.0 mL DMF and stirred overnight at RT. The reaction mixture was purified by preparative HPLC. The product-containing fractions were combined and freeze-dried.

Workup

  1. customThe reaction mixture was purified by preparative HPLC
  2. customfreeze-dried

Sources & evidence

ORD record
ord-efabdbbf1c06485481fecc2d496445e5
Source dataset
uspto-grants-2015_02
Patent number
US08952014B2

Reaction notes

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