Trifluoroacetic acid → HCID 58456382, compound

HRID 410666Notes

Reaction equation

HRID 410666 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1([C:13]2[S:14][C:15]([C:18]3[CH:19]=[C:20]([N:25]([C:33]4[N:38]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:36]=[CH:35][N:34]=4)C(=O)OC(C)(C)C)[CH:21]=[C:22]([CH3:24])[CH:23]=3)=[CH:16][N:17]=2)[CH2:11][CH2:10][C:9](=[O:12])[NH:8][CH2:7][CH2:6]1.C(O)(C(F)(F)F)=O>C(#N)C.O>[OH:1][CH2:2][CH2:3][O:4][C:5]1([C:13]2[S:14][C:15]([C:18]3[CH:19]=[C:20]([NH:25][C:33]4[N:38]=[C:37]([C:39]([F:40])([F:41])[F:42])[CH:36]=[CH:35][N:34]=4)[CH:21]=[C:22]([CH3:24])[CH:23]=3)=[CH:16][N:17]=2)[CH2:6][CH2:7][NH:8][C:9](=[O:12])[CH2:10][CH2:11]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67261316HCID 67261316, compound

Product 1

HCID 58456382HCID 58456382, compoundYield 79.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
125 °C

Procedure

A bi-phasic mixture of the product from Step 1 (15 mg, 0.02 mmol) in acetonitrile and water with 0.05% TFA (reverse-phase HPLC solvent system) was heated at 125° C. for 10 minutes. The reaction was concentrated in vacuo, and the residual oil was partitioned between EtOAc (2×40 ml) and saturated aqueous NaHCO3 (55 ml). The combined organic layers were dried over MgSO4, filtered and concentrated to afford the desired title product (8.1 mg, 77%) as a yellow oil. MS ESI: [M+H]+ m/z 508.2 1H NMR (500 MHz, DMSO) δ 10.3 (m, 1H), 8.82 (m, 1H), 8.04 (m, 1H), 7.98 (s, 1H), 7.54 (m, 1H), 7.45 (s, 1H), 7.17 (s, 1H), 4.68 (m, 1H), 3.98 (m, 2H), 3.55 (m, 2H), 3.00-2.79 (m, 2H), 2.38 (s, 3H), 2.37-1.82 (m, 3H), 1.37-1.01 (m, 3H). rhSYK activity=+++

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe residual oil was partitioned between EtOAc (2×40 ml) and saturated aqueous NaHCO3 (55 ml)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-81ad3d7f49ac461ea5d6ecc0b14014cf
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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