Trifluoroacetic acid → HCID 71554512, compound

HRID 2283172Notes

Reaction equation

HRID 2283172 reaction equation
[Cl:1][CH:2]([Cl:36])[C:3]([N:5]1[C@H:9]([CH2:10][F:11])[C@@H:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([C@H:24]([NH:26]C(=O)OC(C)(C)C)[CH3:25])=[CH:20][CH:19]=3)=[CH:14][CH:13]=2)[O:7]C1(C)C)=[O:4].C(O)(C(F)(F)F)=O>C(Cl)Cl.C1(C)C=CC=CC=1>[NH2:26][C@@H:24]([C:21]1[CH:22]=[CH:23][C:18]([C:15]2[CH:16]=[CH:17][C:12]([C@@H:8]([OH:7])[C@H:9]([NH:5][C:3](=[O:4])[CH:2]([Cl:36])[Cl:1])[CH2:10][F:11])=[CH:13][CH:14]=2)=[CH:19][CH:20]=1)[CH3:25]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89519227HCID 89519227, compound

Product 1

HCID 71554512HCID 71554512, compoundYield 62.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the product of step 1 (130 mg. 0.241 mmol) in DCM (3 mL) is added TFA (0.7 mL) and stirred at room temperature for 1 hour. Reaction is diluted with toluene (10 mL) and concentrated. The crude product is dissolved in DMF (2 mL) and DIPEA (200 μL), and purified using HPLC eluting from 5% acetonitrile/water to 100 acetonitrile/water to give the title compound (60 mg). 1H NMR (400 MHz, CD3OD) δ 1.69 (d, 3H, J=4.0 Hz), 4.31-4.41 (m, 1.5H), 4.44-4.55 (m, 1.5H) 4.56-4.63 (m, 0.5H), 4.68-4.74 (m, 0.5H), 5.02 (d, 1H, J=4.0 Hz) 6.31 (s, 1H), 7.48-7.57 (m, 4H), 7.63 (d, 2H, J=8.0 Hz), 7.72 (d, 2H, J=8.0 Hz). m/z (Cl) 382 [M-OH].

Workup

  1. customReaction
  2. concentrationconcentrated
  3. dissolutionThe crude product is dissolved in DMF (2 mL)
  4. customDIPEA (200 μL), and purified
  5. washeluting from 5% acetonitrile/water to 100 acetonitrile/water

Sources & evidence

ORD record
ord-88ce3de8f8ba495f97f0ab03ae6797b0
Source dataset
uspto-grants-2015_09
Patent number
US09145355B2

Reaction notes

Loading…