Diisopropylethylamine → 4-methyl-6-(2-methyl-6-(2-oxo-2,3-dihydro-1H-spiro[[1,8]naphthyridin-4,4'-piperidin]-1'-yl)pyrimidin-4-yloxy)benzo[d]oxazol-2(3H)-one

HRID 1846580Notes

Reaction equation

HRID 1846580 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4]2([C:15]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:8](=[O:16])[CH2:7]2)[CH2:3][CH2:2]1.Cl[C:18]1[N:23]=[C:22]([CH3:24])[N:21]=[C:20]([O:25][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)[CH:19]=1.CCN(C(C)C)C(C)C>CN(C=O)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:25][C:20]2[CH:19]=[C:18]([N:1]3[CH2:2][CH2:3][C:4]4([C:15]5[C:10](=[N:11][CH:12]=[CH:13][CH:14]=5)[NH:9][C:8](=[O:16])[CH2:7]4)[CH2:5][CH2:6]3)[N:23]=[C:22]([CH3:24])[N:21]=2)[CH:35]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 591657751H-Spiro[[1,8]naphthyridine-4,4'-piperidin]-2(3H)-oneHCID 86663906HCID 86663906, compound

Product 1

HCID 462439844-methyl-6-(2-methyl-6-(2-oxo-2,3-dihydro-1H-spiro[[1,8]naphthyridin-4,4'-piperidin]-1'-yl)pyrimidin-4-yloxy)benzo[d]oxazol-2(3H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

26 mg (0.12 mmol) 1H-spiro[[1,8]naphthyridin-4,4′-piperidin]-2(3H)-one, 35 mg (0.12 mmol) 6-(6-chloro-2-methylpyrimidin-4-yloxy)-4-methylbenzo[d]oxazol-2(3H)-one and 42 μL (0.24 mmol) DIPEA in 2.0 mL DMF were stirred for 4 days at 60° C. The reaction mixture was purified by preparative HPLC-MS. The fractions containing product were combined and lyophilised.

Workup

  1. customThe reaction mixture was purified by preparative HPLC-MS
  2. additionThe fractions containing product

Sources & evidence

ORD record
ord-e7cb16b39ee443bc80fc5c2d96ea1925
Source dataset
uspto-grants-2015_02
Patent number
US08952014B2

Reaction notes

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