Trifluoroacetic acid → HCID 67200894, compound

HRID 1888523Notes

Reaction equation

HRID 1888523 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([S:14][C:15]2[C:20]3[C:21]4[CH:35]=[C:34]([C:36]5[CH:37]=[N:38][N:39]([CH3:41])[CH:40]=5)[CH:33]=[N:32][C:22]=4[N:23](COCC[Si](C)(C)C)[C:19]=3[CH:18]=[N:17][C:16]=2[C:42]#[N:43])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:41][N:39]1[CH:40]=[C:36]([C:34]2[CH:33]=[N:32][C:22]3[NH:23][C:19]4[CH:18]=[N:17][C:16]([C:42]#[N:43])=[C:15]([S:14][CH:11]5[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]5)[C:20]=4[C:21]=3[CH:35]=2)[CH:37]=[N:38]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58266610HCID 58266610, compound

Product 1

HCID 67200894HCID 67200894, compoundYield 32.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-[6-cyano-3-(1-methyl-1H-pyrazol-4-yl)-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrol-5-ylsulfanyl]piperidine-1-carboxylic acid tert-butyl ester (106 mg, 0.17 mmol) and trifluoroacetic acid (1 mL) in dichloromethane (9 mL) was stirred at ambient temperature for 22 h. The reaction mixture was concentrated in vacuo and the resultant residue partitioned between dichloromethane (10 mL) and a saturated aqueous solution of sodium hydrogen carbonate (10 mL). The organic phase was concentrated in vacuo and the residue was adsorbed onto HM-N then purified by flash chromatography (silica, 25 g column, Si-SPE, 0-13% (2M ammonia in MeOH) in DCM) to afford the title compound as a pale yellow solid (21.5 mg, 25%). 1H NMR (DMSO-D6, 300 MHz): 9.04 (d, J=2.2 Hz, 1H), 9.02-8.97 (m, 2H), 8.29 (s, 1H), 7.98 (s, 1H), 3.93 (s, 3H), 3.54-3.21 (m, 1H), 2.97-2.86 (m, 2H), 2.49-2.36 (m, 2H), 1.89-1.77 (m, 2H), 1.65-1.47 (m, 2H). LCMS (Method F): RT=7.08 min, M+H+=390.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe resultant residue partitioned between dichloromethane (10 mL)
  3. concentrationThe organic phase was concentrated in vacuo
  4. customthen purified by flash chromatography (silica, 25 g column, Si-SPE, 0-13% (2M ammonia in MeOH) in DCM)

Sources & evidence

ORD record
ord-e19734982882440bbfb2223147a7034d
Source dataset
uspto-grants-2013_08
Patent number
US08501765B2

Reaction notes

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