Diisopropylethylamine → HCID 44476490, compound

HRID 2192522Notes

Reaction equation

HRID 2192522 reaction equation
[CH3:1][C:2]([O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][CH:7]=1)([CH3:4])[CH3:3].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.O[NH:49][C:50]([C:52]1[C:53]2[CH:54]=[CH:55][N:56]=[CH:57][C:58]=2[CH:59]=[CH:60][CH:61]=1)=[NH:51]>CN(C)C=O>[CH3:4][C:2]([O:5][C:6]1[CH:7]=[CH:8][C:9]([C:10]2[O:12][N:51]=[C:50]([C:52]3[CH:61]=[CH:60][CH:59]=[C:58]4[C:53]=3[CH:54]=[CH:55][N:56]=[CH:57]4)[N:49]=2)=[CH:13][CH:14]=1)([CH3:1])[CH3:3]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5353024-tert-Butoxybenzoic AcidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178513273HCID 178513273, compound

Product 1

HCID 44476490HCID 44476490, compoundYield 18.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 4-[(1,1-dimethylethyl)oxy]benzoic acid (Apin chemicals) (117 mg, 0.603 mmol), HATU (232 mg, 0.610 mmol), Hunig's base (0.263 mL, 1.506 mmol) in N,N-Dimethylformamide (DMF) (1 ml) was stirred for 1 hr before the addition of N-hydroxy-5-isoquinolinecarboximidamide (D1; 94 mg, 0.502 mmol) in N,N-dimethylformamide (DMF) (1 ml). The reaction was left to stir at room temperature for 2 hrs and then heated to 120° C. for 2 hr in the microwave. The reaction mixture was concentrated in vacuo and purified by preparative HPLC (Waters Sunfire C18 column, eluting with solvents A/B (A: Water+0.1% Formic acid, B: MeCN+0.1% Formic acid)) to give the title compound (31.5 mg)

Workup

  1. waitThe reaction was left
  2. temperatureheated to 120° C. for 2 hr in the microwave
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. custompurified by preparative HPLC (Waters Sunfire C18 column
  5. washeluting with solvents A/B (A: Water+0.1% Formic acid, B

Sources & evidence

ORD record
ord-88f60357fcee486da1078e71f424c625
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

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