Trifluoroacetic acid → HCID 90386182, compound

HRID 2170180Notes

Reaction equation

HRID 2170180 reaction equation
[C:1]1([C:7]2[CH:8]=[CH:9][N:10]3[C:15]=2[C:14]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)=[N:13][C:12]([C:24]2([NH:27]C(=O)OC(C)(C)C)[CH2:26][CH2:25]2)=[N:11]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:27][C:24]1([C:12]2[N:13]=[C:14]([NH:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[C:15]3=[C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH:8]=[CH:9][N:10]3[N:11]=2)[CH2:25][CH2:26]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90396873HCID 90396873, compound

Product 1

HCID 90386182HCID 90386182, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl (1-(5-phenyl-4-((pyridin-2-ylmethyl)amino) pyrrolo[2,1-f][1,2,4]triazin-2-yl)cyclopropyl)carbamate (200 mg, 0.438 mmol) in DCM (15 mL) was added TFA (0.169 mL, 2.19 mmol) and the reaction mixture was stirred at RT for 5 h then concentrated under reduced pressure. The residue was dissolved in (100 mL) and washed with 10% NaHCO3 solution (2×30 mL). The combined organic portion was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified using CombiFlash ISCO (REDISEP®, SiO2, 12 g, 50% EtOAc/petroleum ether) to give 2-(1-aminocyclopropyl)-5-phenyl-N-(pyridin-2-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine (120 mg, 77.0%) as brown solid. LCMS Condition B-41: retention time 0.62 min, [M+1]=357.1. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.80-0.87 (m, 2H), 1.13-1.18 (m, 2H), 4.68 (d, J=4.8 Hz, 2H), 6.68 (d, J=2.7 Hz, 1H), 7.02 (s, 1H), 7.22-7.30 (m, 1H), 7.35 (d, J=7.8 Hz, 1H), 7.41-7.58 (m, 5H), 7.68-7.80 (m, 2H), 8.34-8.40 (m, 1H).

Workup

  1. concentrationthen concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in (100 mL)
  3. washwashed with 10% NaHCO3 solution (2×30 mL)
  4. dry with materialThe combined organic portion was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified

Sources & evidence

ORD record
ord-a7c4e66de65f41e8afa508a203511040
Source dataset
uspto-grants-2015_06
Patent number
US09050345B2

Reaction notes

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