Diisopropylethylamine → HCID 44609944, compound

HRID 1398011Notes

Reaction equation

HRID 1398011 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:8]=2/[CH:9]=[C:10]2/[C:11](=[O:16])[NH:12][C:13](=[O:15])[S:14]/2)[CH2:3]1.[CH3:22][N:23]1[CH:27]=[CH:26][N:25]=[C:24]1[C:28](O)=[O:29].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>ClCCl>[Cl:21][C:20]1[CH:19]=[CH:18][CH:17]=[C:8](/[CH:9]=[C:10]2/[C:11](=[O:16])[NH:12][C:13](=[O:15])[S:14]/2)[C:7]=1[N:4]1[CH2:5][CH2:6][C@H:2]([NH:1][C:28]([C:24]2[N:23]([CH3:22])[CH:27]=[CH:26][N:25]=2)=[O:29])[CH2:3]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5576781-methyl-1H-imidazole-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58423275HCID 58423275, compound

Product 1

HCID 44609944HCID 44609944, compoundYield 21.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 50 mL vial charged with a magnetic stir bar was added (S,Z)-5-(2-(3-aminopyrrolidin-1-yl)-3-chlorobenzylidene)thiazolidine-2,4-dione (75 mg, 0.23 mmol) (Example 86), 1-methyl-1H-imidazole-2-carboxylic acid (87 mg, 0.69 mmol), HATU (220 mg, 0.58 mmol) and dichloromethane (5 mL). Hunig's base (0.202 mL, 1.16 mmol) was then added and the mixture was stirred at rt for 4 h. The reaction was then diluted with dichloromethane and washed with water. The mixture was separated with a phase separator tube and the organic phase was evaporated to dryness. The residue was purified by reverse phase chromatography to afford the title compound as a yellow solid (21 mg, 21%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.89 (s, 1 H) 7.51 (dd, 1 H) 7.41 (dd, 1 H) 7.18-7.27 (m, 2 H) 7.01 (s, 1 H) 4.67-4.77 (m, 1 H) 4.00 (s, 3 H) 3.63-3.75 (m, 2 H) 3.47-3.54 (m, 1 H) 3.36-3.47 (m, 1 H) 2.39-2.51 (m, 1 H) 2.14 (dd, 1 H); m/z 432.

Workup

  1. additionTo a 50 mL vial charged with a magnetic stir bar
  2. washwashed with water
  3. customThe mixture was separated with a phase separator tube
  4. customthe organic phase was evaporated to dryness
  5. customThe residue was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-b9e2f6ebbaa64489982b70af08092a93
Source dataset
uspto-grants-2014_12
Patent number
US08901307B2

Reaction notes

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