Acetic Acid → HCID 44609577, compound

HRID 2094206Notes

Reaction equation

HRID 2094206 reaction equation
[NH2:1][C:2]([NH:4][C:5]1[NH:6][C:7]2[C:12]([C:13]=1[C:14]([NH2:16])=[O:15])=[CH:11][CH:10]=[C:9]([O:17][C:18]1[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=1)[CH:8]=2)=[O:3].[C:25](O)(=[O:27])[CH3:26].C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C)C=O.O>[C:25]([NH:24][C:21]1[CH:22]=[CH:23][C:18]([O:17][C:9]2[CH:8]=[C:7]3[C:12]([C:13]([C:14]([NH2:16])=[O:15])=[C:5]([NH:4][C:2]([NH2:1])=[O:3])[NH:6]3)=[CH:11][CH:10]=2)=[CH:19][CH:20]=1)(=[O:27])[CH3:26]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67071861HCID 67071861, compound

Product 1

HCID 44609577HCID 44609577, compoundYield 47.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The solution of 2-aminocarbonylamino-6-(4-aminophenyloxy)indole-3-carboxamide (Compound No.5-1, 40 mg, 0.12 mmol), acetic acid (8 μL, 0.14 mmol), N,N-diisopropylethylamine (46 μL, 0.26 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (48 mg, 0.13 mmol) in anhydrous N,N-dimethylformamide (1 mL) was stirred overnight at room temperature. Water (10 mL) was added to the reaction solution, and the precipitated solid was filtered off and washed with water (10 mL). The solid was dried at 40° C. under reduced pressure to give the title compound (21 mg) as a purple solid (46%).

Workup

  1. filtrationthe precipitated solid was filtered off
  2. washwashed with water (10 mL)
  3. customThe solid was dried at 40° C. under reduced pressure

Sources & evidence

ORD record
ord-37749bfdf1274fe58105149fcf35d5cb
Source dataset
uspto-grants-2013_05
Patent number
US08445529B2

Reaction notes

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