Dimethylformamide → HCID 24760964, compound

HRID 1161300Notes

Reaction equation

HRID 1161300 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]([CH2:13][CH2:14][NH:15][C:16](=[O:18])[CH3:17])[C:7]2=[O:12].[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27](O)=[O:28])=[CH:22][C:21]=1[F:30].F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.CN(C)C=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:16]([NH:15][CH2:14][CH2:13][N:6]1[CH:5]=[CH:4][C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[NH:1][C:27](=[O:28])[CH2:26][C:23]2[CH:24]=[CH:25][C:20]([Cl:19])=[C:21]([F:30])[CH:22]=2)[C:7]1=[O:12])(=[O:18])[CH3:17]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 38149542-(4-Chloro-3-fluorophenyl)acetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59515672HCID 59515672, compound

Product 1

HCID 24760964HCID 24760964, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

Into a 20 ml reaction vial was combined N-(2-(5-amino-1-oxoisoquinolin-2(1H)-yl)ethyl)acetamide (20 mg, 0.00008 mol), 2-(4-chloro-3-fluorophenyl)acetic acid (30.55 mg, 0.0001620 mol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (72.66 mg, 0.0001911 mol) N,N-diisopropylethylamine (61.6 μL, 0.000353 mol), and N,N-dimethylformamide (1 mL, 0.02 mol). The mixture was heated at 50° C. for two hours, allowed to cool and poured onto sat sodium bicarbonate (200 ml). The mixture was extraced with methylene chloride (3×100 ml). The combined extracts were dried over sodium sulfate and reduced in vacuo. The mixture was purified by reverse phase prep HPLC using an acetonitrile:water gradient at pH 10. The combined pure fractions were reduced in vacuo to yield the compound as an off white solid.

Workup

  1. customInto a 20 ml reaction
  2. temperatureto cool
  3. additionpoured
  4. dry with materialThe combined extracts were dried over sodium sulfate
  5. customThe mixture was purified by reverse phase prep HPLC
  6. customto yield the compound as an off white solid

Sources & evidence

ORD record
ord-30ea5986c2404d589339498a542e6860
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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