Morpholine → HCID 178506134, compound

HRID 1725597Notes

Reaction equation

HRID 1725597 reaction equation
[CH2:1]([C:5]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]([F:20])([F:19])[F:18])[N:8]=[C:7]([NH:21][C:22]2[C:30]3[C:25](=[N:26][CH:27]=[CH:28][CH:29]=3)[NH:24][N:23]=2)[CH:6]=1)[CH2:2][CH:3]=C.O=[O+][O-].[NH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO.O1CCCC1>[N:34]1([CH2:3][CH2:2][CH2:1][C:5]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:17]([F:19])([F:18])[F:20])[N:8]=[C:7]([NH:21][C:22]3[C:30]4[C:25](=[N:26][CH:27]=[CH:28][CH:29]=4)[NH:24][N:23]=3)[CH:6]=2)[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1

Participants

7

Reactant 4

HCID 8083Morpholine2×HCID 24823OzoneHCID 5049666Sodium triacetoxyborohydride2×HCID 178441137HCID 178441137, compound

Product 1

HCID 178506134HCID 178506134, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of [6-but-3-enyl-2-(2-trifluoromethyl-phenyl)-pyrimidin-4-yl]-(1H-pyrazolo[3,4-b]pyridin-3-yl)-amine (0.10 g, 0.25 mmol) in methanol (5 mL) and tetrahydrofuran (5 mL) at −78° C. was bubbled through with ozone for 5 minutes. To this mixture was added morpholine (0.05 mL, 0.56 mmol) and sodium triacetoxyborohydride (0.39 g, 1.85 mmol). The reaction was stirred at room temperature for 24 hours when additional morpholine (0.10 mL, 1.28 mmol) and sodium triacetoxyborohydride (0.39 g, 1.85 mmol) were added then the stirring continued another 2 hours. The reaction was quenched with sodium bicarbonate and evaporated. Purification by flash chromatography (SiO2, eluted with 1:9 methanol:dichloromethane), followed by preparative HPLC provided the title compound as a bright yellow lyophilate (0.068 g, 38% yield). 484.3 (M+H). 1H-NMR (500 MHz, DMSO-d6) δ 13.2 (s, 1H), 10.7 (s, 1H), 9.60 (br s, 1H), 8.52 (m, 1H), 8.47 (d, 1H), 7.86 (d, 1H), 7.77 (m, 1H), 7.70 (m, 2H), 7.14 (m, 1H), 3.97 (br m, 2H), 3.61 (br m, 2H), 3.44 (br m, 2H), 3.18 (br m, 2H), 3.05 (br m, 2H), 2.78 (t, 2H), 2.08 (m, 2H) ppm.

Workup

  1. additionwere added
  2. customThe reaction was quenched with sodium bicarbonate
  3. customevaporated
  4. customPurification
  5. washby flash chromatography (SiO2, eluted with 1:9 methanol:dichloromethane)

Sources & evidence

ORD record
ord-1c64cb2a96244cc1a19f2d3ad2885515
Source dataset
uspto-grants-2009_02
Patent number
US07491730B2

Reaction notes

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