Diisopropylethylamine → HCID 44476574, compound

HRID 2192524Notes

Reaction equation

HRID 2192524 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:15])[C:10]=1[O:11][CH2:12][CH2:13][CH3:14])[C:5]([OH:7])=O.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:50][C:51]([C:53]1[C:54]2[CH:55]=[CH:56][N:57]=[CH:58][C:59]=2[CH:60]=[CH:61][CH:62]=1)=[NH:52]>CN(C)C=O>[Cl:15][C:9]1[CH:8]=[C:4]([C:5]2[O:7][N:52]=[C:51]([C:53]3[CH:62]=[CH:61][CH:60]=[C:59]4[C:54]=3[CH:55]=[CH:56][N:57]=[CH:58]4)[N:50]=2)[CH:3]=[C:2]([Cl:1])[C:10]=1[O:11][CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 27430763,5-dichloro-4-propoxybenzoic 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 44476574HCID 44476574, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 3,5-dichloro-4-(propyloxy)benzoic acid, (Maybridge) (150 mg, 0.603 mmol), HATU (232 mg, 0.610 mmol), Hunig's base (0.263 mL, 1.506 mmol) and 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 mixture was left to stir for 2 hrs at room temperature and then heated to 120° C. for 2 hr in a microwave. The cooled reaction mixture was concentrated in vacuo and the residue purified by Mass Directed Preparative HPLC (Supelcosil ABZ+Plus column, eluting with solvents A/B (A: Water+0.1% Formic acid, B: MeCN:Water 95:5+0.05% Formic acid)) to give the title compound (23 mg)

Workup

  1. waitThe reaction mixture was left
  2. temperatureheated to 120° C. for 2 hr in a microwave
  3. customThe cooled reaction mixture
  4. concentrationwas concentrated in vacuo
  5. customthe residue purified by Mass Directed Preparative HPLC (Supelcosil ABZ+Plus column
  6. washeluting with solvents A/B (A: Water+0.1% Formic acid, B

Sources & evidence

ORD record
ord-9cef3fa1f643414f86b4533a7a0e0f3a
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

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