Diisopropylethylamine → HCID 25265434, compound

HRID 2096370Notes

Reaction equation

HRID 2096370 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][C:5]2([O:12][C:11](=[O:13])[NH:10][C:9]3[CH:14]=[CH:15][CH:16]=[CH:17][C:8]2=3)[CH2:4][CH2:3]1.Cl[C:19]1[N:24]=[CH:23][N:22]=[C:21]([C:25]([C:27]2[CH:36]=[C:35]([CH3:37])[C:30]3[NH:31][C:32](=[O:34])[O:33][C:29]=3[CH:28]=2)=[O:26])[CH:20]=1.[CH3:38]CN(C(C)C)C(C)C>CN(C=O)C>[CH3:38][N:31]1[C:30]2[C:35]([CH3:37])=[CH:36][C:27]([C:25]([C:21]3[N:22]=[CH:23][N:24]=[C:19]([N:2]4[CH2:3][CH2:4][C:5]5([O:12][C:11](=[O:13])[NH:10][C:9]6[CH:14]=[CH:15][CH:16]=[CH:17][C:8]5=6)[CH2:6][CH2:7]4)[CH:20]=3)=[O:26])=[CH:28][C:29]=2[O:33][C:32]1=[O:34]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 13050640Spiro[3,1-benzoxazine-4,4'-piperidin]-2(1H)-one--hydrogen chloride (1/1)HCID 581812066-(6-chloropyrimidine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one

Product 1

HCID 25265434HCID 25265434, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

102 mg (0.400 mmol) spiro[benzo[d][1,3]oxazin-4,4′-piperidin]-2(1H)-on hydrochloride, 122 mg (0.400 mmol) 6-(6-chloropyrimidin-4-carbonyl)-4-methyl-3H-benzoxazol-2-one and 0.210 mL (1.20 mmol) DIPEA were combined in 3.0 mL DMF and stirred for 48 h. The mixture was purified by preparative HPLC-MS. The fractions containing the product were combined, the organic solvent was eliminated i.vac. and the aqueous phase remaining was neutralised with 4M aqueous NaOH solution. The product precipitated as a solid was suction filtered, washed with water and dried in the CAD.

Workup

  1. customThe mixture was purified by preparative HPLC-MS
  2. additionThe fractions containing the product
  3. customThe product precipitated as a solid
  4. filtrationfiltered
  5. washwashed with water
  6. customdried in the CAD

Sources & evidence

ORD record
ord-cd3eb2b522824227bec5e9f79cebcc8f
Source dataset
uspto-grants-2013_05
Patent number
US08450327B2

Reaction notes

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