Trifluoroacetic acid → HCID 58300064, compound

HRID 79121Notes

Reaction equation

HRID 79121 reaction equation
[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([NH:15][C:16]4[N:21]=[CH:20][C:19]([N:22]5[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]5)=[CH:18][C:17]=4[CH3:35])[N:13]=[CH:14][C:9]=3[C:8]3[CH:36]=[CH:37][N:38]=[CH:39][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl.O>[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([NH:15][C:16]4[C:17]([CH3:35])=[CH:18][C:19]([N:22]5[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]5)=[CH:20][N:21]=4)[N:13]=[CH:14][C:9]=3[C:8]3[CH:36]=[CH:37][N:38]=[CH:39][C:7]2=3)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 582996341,1-dimethylethyl 4-(6-((9-cyclopentyl-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)-5-methyl-3-pyridinyl)-1-piperazinecarboxylate

Product 1

HCID 58300064HCID 58300064, compoundYield 40.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

Compound 78 (0.100 g, 0.189 mmol) was dissolved in DCM (3 mL) followed by TFA (1 mL) and stirred at 40° C. in a water bath for 30 min. Concentration under vacuum provided a yellowish oil which was partially dissolved in water and then filtered. The filtrate was purified by preparative RP-HPLC eluting with a gradient of 5% MeCN/water/0.1% TFA-30% MeCN/water/0.1% TFA to yield compound 76 as a yellow solid (33 mg). 1H NMR (500 MHz, DMSO-d6) δ 10.18 (1H, s), 9.51 (1H, s), 9.31 (1H, s), 8.95 (2H, br s), 8.65 (1H, d, J=6.2 Hz), 8.55 (1H, d, J=6.1 Hz), 8.12 (1H, d, J=3.0), 7.58 (1H, d, J=2.4 Hz), 5.25 (1H, p, J=8.3 Hz), 3.46 (4H, t, J=5.4 Hz), 3.30 (4H, m), 2.24 (3H, s), 2.18 (2H, m), 2.01 (2H, m), 1.70 (2H, m), 1.55 (2H, m) ppm; LCMS-ESI (POS), M/Z, M+1: Found 429.2.

Workup

  1. concentrationConcentration under vacuum
  2. customprovided a yellowish oil which
  3. filtrationfiltered
  4. customThe filtrate was purified by preparative RP-HPLC
  5. washeluting with a gradient of 5% MeCN/water/0.1% TFA-30% MeCN/water/0.1% TFA

Sources & evidence

ORD record
ord-eb239c34d447442da1763fb298ef0121
Source dataset
uspto-grants-2014_09
Patent number
US08841312B2

Reaction notes

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