Diisopropylethylamine → HCID 25268019, compound

HRID 469375

Reaction equation

HRID 469375 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:11]3[CH:12]=[N:13][C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=4[C:10]=3[NH:9][C:8]2=[O:20])[CH2:3][CH2:2]1.Cl[C:22]1[N:27]=[CH:26][N:25]=[C:24]([C:28]([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)=[O:29])[CH:23]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:40][C:38]1[C:33]2[NH:34][C:35](=[O:37])[O:36][C:32]=2[CH:31]=[C:30]([C:28]([C:24]2[N:25]=[CH:26][N:27]=[C:22]([N:1]3[CH2:2][CH2:3][CH:4]([N:7]4[C:11]5[CH:12]=[N:13][C:14]6[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=6[C:10]=5[NH:9][C:8]4=[O:20])[CH2:5][CH2:6]3)[CH:23]=2)=[O:29])[CH:39]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 183215593-Piperidin-4-yl-1,3-dihydroimidazo[4,5-c]quinolin-2-oneHCID 581812066-(6-chloropyrimidine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one

Product 1

HCID 25268019HCID 25268019, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

134 mg (0.500 mmol) 3-piperidin-4-yl-1,3-dihydroimidazo[4,5-c]quinolin-2-one, 145 mg (0.500 mmol) 6-(6-chloropyrimidine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one and 0.174 mL (1.00 mmol) DIPEA were stirred overnight in 5 mL DMF at RT. 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 a 4N aqueous NaOH solution. The precipitate 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. filtrationfiltered
  4. washwashed with water
  5. customdried in the CAD

Sources & evidence

ORD record
ord-da5814286f254d6786db46861f03167f
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Linked notes

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