Morpholine → 3-(2-Fluorophenyl)-5-[4-(morpholin-4-yl)piperidin-1-yl]-[1,2,3]triazolo[1,5-a]quinazoline

HRID 1581633Notes

Reaction equation

HRID 1581633 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[F:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]1[N:23]=[N:24][N:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:28]([N:35]3[CH2:40][CH2:39][C:38](=O)[CH2:37][CH2:36]3)=[N:27][C:26]=12.[NH:42]1[CH2:47][CH2:46][O:45][CH2:44][CH2:43]1>C(Cl)Cl>[F:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]1[N:23]=[N:24][N:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:28]([N:35]3[CH2:36][CH2:37][CH:38]([N:42]4[CH2:47][CH2:46][O:45][CH2:44][CH2:43]4)[CH2:39][CH2:40]3)=[N:27][C:26]=12

Participants

5

Reactant 3

HCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 99251083-(2-Fluorophenyl)-5-(4-oxopiperidin-1-yl)-[1,2,3]triazolo[1,5-a]quinazoline

Product 1

HCID 101376683-(2-Fluorophenyl)-5-[4-(morpholin-4-yl)piperidin-1-yl]-[1,2,3]triazolo[1,5-a]quinazolineYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Sodium triacetoxyborohydride (0.53 g, 2.75 mmol) was added portionwise over 10 min to a solution of 3-(2-fluorophenyl)-5-(4-oxopiperidin-1-yl)-[1,2,3]triazolo[1,5-α]quinazoline (0.30 g, 0.83 mmol) and morpholine (0.36 g, 4.1 mmol) in CH2Cl2 (5 ml) and the mixture was allowed to stir for a further 48 h. The mixture was diluted with CH2Cl2 (150 ml), washed with water (50 ml) and brine (50 ml), dried over MgSO4 and evaporated to give a yellow oil. Purification by flash column chromatography on silica eluting with CH2Cl2:MeOH (98:2) followed by trituration with diethyl ether gave 3-(2-fluorophenyl)-5-[4-(morpholin-4-yl)piperidin-1-yl]-[1,2,3]triazolo[1,5-α]quinazoline (0.255 g, 71%) as a white solid. δH (400 MHz; CDCl3) 1.78-1.88 (2H, m), 2.04-2.08 (2H, m), 2.43-2.53 (1H, m), 2.58-2.68 (4H, m), 3.07-3.14 (2H, m), 3.75-3.78 (4H, m), 4.17-4.22 (2H, m), 7.19-7.30 (2H, m), 7.33-7.39 (1H, m), 7.61 (1H, ddd, J=8, 8 and 1), 7.88 (1H, ddd, J=8, 8 and 1), 8.00 (1H, d, J=8), 8.13 (1H, ddd, J=7, 7 and 2), 8.69 (1H, d, J=8); m/z (ES+) 433 (M+H+).

Workup

  1. washwashed with water (50 ml) and brine (50 ml)
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customto give a yellow oil
  5. customPurification by flash column chromatography on silica eluting with CH2Cl2:MeOH (98:2)

Sources & evidence

ORD record
ord-94c90dbdae9a4f2894409d5c86bd85f0
Source dataset
uspto-grants-2004_05
Patent number
US06730681B2

Reaction notes

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