Morpholine → HCID 58976695, compound

HRID 601054Notes

Reaction equation

HRID 601054 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:15]=[CH:14][C:10]([C:11](O)=[O:12])=[CH:9][CH:8]=2)[N:5]=[C:4]([NH:16][C:17]2[CH:25]=[CH:24][C:20]3[O:21][CH2:22][O:23][C:19]=3[CH:18]=2)[N:3]=1.[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C1COCC1.O>[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[CH:9][C:10]([C:11]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[O:12])=[CH:14][CH:15]=2)[N:5]=[C:4]([NH:16][C:17]2[CH:25]=[CH:24][C:20]3[O:21][CH2:22][O:23][C:19]=3[CH:18]=2)[N:3]=1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 672740044-[5-Amino-3-(benzo[1,3]dioxol-5-ylamino)-[1,2,4]triazol-1-yl]-benzoic acid

Product 1

HCID 58976695HCID 58976695, compoundYield 5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-[5-amino-3-(benzo[1,3]dioxol-5-ylamino)-[1,2,4]triazol-1-yl]-benzoic acid (0.15 g, 0.44 mmol), morpholine (0.05 mL, 0.55 mmol) and HBTU (0.21 g, 0.55 mmol) in THF (5 mL) was stirred at room temperature for 4 h. The reaction was diluted with water, extracted with methanol/dichloromethane, dried (sodium sulfate) and evaporated. Purification by 2 successive semi-preparative HPLC's provided the title compound (0.008 g, 5% yield) as a pale pink lyophilate.

Workup

  1. extractionextracted with methanol/dichloromethane
  2. dry with materialdried (sodium sulfate)
  3. customevaporated
  4. customPurification by 2 successive semi-preparative HPLC's

Sources & evidence

ORD record
ord-cfd2fd44f20b478790a55487187a6185
Source dataset
uspto-grants-2011_03
Patent number
US07902239B2

Reaction notes

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