Diisopropylethylamine → HCID 50991923, compound

HRID 2192270Notes

Reaction equation

HRID 2192270 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:17]=[C:16]3[C:12]([C:13]([C:26]4[CH:34]=[CH:33][C:29]([C:30]([O-:32])=O)=[CH:28][CH:27]=4)=[CH:14][N:15]3[C:18]3[CH:23]=[C:22]([NH:24][CH3:25])[N:21]=[CH:20][N:19]=3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[O:35]1[CH2:40][CH2:39][N:38]([CH2:41][CH2:42][NH2:43])[CH2:37][CH2:36]1.C(N(C(C)C)CC)(C)C.C(=O)(O)[O-].[Na+]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:17]=[C:16]3[C:12]([C:13]([C:26]4[CH:34]=[CH:33][C:29]([C:30]([NH:43][CH2:42][CH2:41][N:38]5[CH2:39][CH2:40][O:35][CH2:36][CH2:37]5)=[O:32])=[CH:28][CH:27]=4)=[CH:14][N:15]3[C:18]3[CH:23]=[C:22]([NH:24][CH3:25])[N:21]=[CH:20][N:19]=3)=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 4082852-MorpholinoethylamineHCID 516892Sodium BicarbonateHCID 50991845HCID 50991845, compound

Product 1

HCID 50991923HCID 50991923, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

O-(7-Azabenzotriazol-1-yl)-N,N,N,N-tetramethyluronium hexafluorophosphate (HATU; 63 mg, 0.167 mmol) was added to a mixture solution of 4-(6-(4-methoxyphenyl)-1-(6-(methylamino)pyrimidin-4-yl)-1H-indol-3-yl)benzoate (50 mg, 0.111 mmol), 2-morpholinoethanamine (14.6 μL, 0.111 mmol) and diisopropylethylamine (DIPEA; 29 μL, 0.167 mmol) in THF (2 mL) at room temperature. 2 hours later, the mixture was added to saturated sodium bicarbonate aqueous solution and then extracted with methylene chloride. The collected organic layer was washed with brine and concentrated under reduced pressure by drying with anhydrous magnesium sulfate. The residue was purified by chromatography (preparative HPLC). The target compound (15 mg) was obtained as white solid.

Workup

  1. extractionextracted with methylene chloride
  2. washThe collected organic layer was washed with brine
  3. concentrationconcentrated under reduced pressure
  4. dry with materialby drying with anhydrous magnesium sulfate
  5. customThe residue was purified by chromatography (preparative HPLC)

Sources & evidence

ORD record
ord-2f0d573c8ef64762ae042ea1c501e4ce
Source dataset
uspto-grants-2012_12
Patent number
US08329708B2

Reaction notes

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