Triethylamine → HCID 24968984, compound

HRID 2381981Notes

Reaction equation

HRID 2381981 reaction equation
C(Cl)(=O)C(Cl)=O.[C:7]1([C:13]2[N:18]=[CH:17][C:16]([C:19]([OH:21])=O)=[CH:15][N:14]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[NH2:22][N:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25][CH2:24]1.C(N(CC)CC)C>C(Cl)Cl>[N:23]1([NH:22][C:19]([C:16]2[CH:17]=[N:18][C:13]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)=[N:14][CH:15]=2)=[O:21])[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 7473892-Phenylpyrimidine-5-carboxylic acidHCID 27609322,3-dihydro-1H-indol-1-amine

Product 1

HCID 24968984HCID 24968984, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride in DCM (2 M, 1.5 mL) is added to a solution of 2-phenyl-pyrimidine-5-carboxylic acid (200 mg, 2 mmol) in DCM (20 mL) and stirred at rt for 2 h. The reaction solution is concentrated in vacuo. The residue is dissolved in DCM (20 mL). N-amino-indoline (268 mg, 2 mmol) and triethylamine (404 mg, 4 mmol) are added and stirred at rt overnight. The mixture is concentrated in vacuo and the residue is purified by silica gel column chromatography eluting with 0-40% EtOAc in heptane to afford 2-phenyl-pyrimidine-5-carboxylic acid (2,3-dihydro-indol-1-yl)-amide (195 mg, 31%) as a solid. MS: 317 (M+H); 1H NMR (300 MHz, CD3OD): δ 3.07 (t, 2H), 3.77 (t, 2H), 6.76 (m, H), 6.82-6.95 (m, H) 7.09-7.24 (m, 2H), 7.54-7.63 (m, 3H), 8.52 (d, 2H), 9.28 (s, 2H) and 2-phenyl-pyrimidine-5-carboxylic acid (indol-1-yl)-amide (10 mg, 2%). MS: 315 (M+H). IC50=2 nM.

Workup

  1. concentrationThe reaction solution is concentrated in vacuo
  2. dissolutionThe residue is dissolved in DCM (20 mL)
  3. stirringstirred at rt overnight
  4. concentrationThe mixture is concentrated in vacuo
  5. customthe residue is purified by silica gel column chromatography
  6. washeluting with 0-40% EtOAc in heptane

Sources & evidence

ORD record
ord-bd8353e8dc854197adf5fc3a80ba8d44
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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