Triethylamine → HCID 21897799, compound

HRID 1864103Notes

Reaction equation

HRID 1864103 reaction equation
C(Cl)(=O)C(Cl)=O.[Br:7][C:8]1[O:12][C:11]([C:13]([OH:15])=O)=[CH:10][CH:9]=1.Cl.[F:17][C:18]1[CH:23]=[C:22]([S:24]([CH3:27])(=[O:26])=[O:25])[CH:21]=[CH:20][C:19]=1[N:28]1[C:32]2=[N:33][CH:34]=[N:35][C:36]([S:37][CH:38]3[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]3)=[C:31]2[CH:30]=[N:29]1.C(N(CC)CC)C>ClCCl.CN(C=O)C>[Br:7][C:8]1[O:12][C:11]([C:13]([N:41]2[CH2:42][CH2:43][CH:38]([S:37][C:36]3[N:35]=[CH:34][N:33]=[C:32]4[N:28]([C:19]5[CH:20]=[CH:21][C:22]([S:24]([CH3:27])(=[O:25])=[O:26])=[CH:23][C:18]=5[F:17])[N:29]=[CH:30][C:31]=34)[CH2:39][CH2:40]2)=[O:15])=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 685115-Bromo-2-furanecarboxylic acidHCID 21897830HCID 21897830, compound

Product 1

HCID 21897799HCID 21897799, compoundYield 48.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (0.51 mmol, 45 μL) and DMF (catalytic amount) were added to 5-bromo-furan-2-carboxylic acid (0.18 mmol, 36 mg) in dichloromethane (3 mL). The reaction mixture was stirred for 40 minutes at room temperature. The organic solvents were removed in vaccuo. The concentrate was re-dissolved in dichloromethane and 1-(2-fluoro-4-methanesulfonyl-phenyl)-4-(piperidin-4-ylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidine hydrochloride (0.16 mmol, 70 mg) and triethylamine (0.47 mmol, 66 μL) were added and stirred for 1.5 hours at room temperature. The progress of the reaction was monitored by thin layer chromatography and LCMS. Purification by HPLC provided Compound A115 as a white solid (45 mg, 41%). 1H NMR (400 MHz, CDCl3) δ (ppm): 8.74 (s, 1H); 8.25 (s, 1H); 7.87 (m, 3H); 7.00 (d, 1H); 6.49 (s, 1H); 4.50 (h, 1H); 4.34 (m, 2H); 3.42 (s broad, 2H); 2.70 (s, 3H); 2.28 (m, 2H); 1.85 (m, 2H). Exact mass calculated for C22H19BrFN5O4S2 580.45, found 582.3 (MH+).

Workup

  1. customThe organic solvents were removed in vaccuo
  2. dissolutionThe concentrate was re-dissolved in dichloromethane
  3. stirringstirred for 1.5 hours at room temperature
  4. customPurification by HPLC

Sources & evidence

ORD record
ord-316e3aeac2ec4ef794fadbaa92bca122
Source dataset
uspto-grants-2009_12
Patent number
US07625906B2

Reaction notes

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