Trifluoroacetic acid → HCID 59394479, compound

HRID 45084Notes

Reaction equation

HRID 45084 reaction equation
C(OC([N:8]1[CH2:17][CH2:16][C:15]2[C:14]([O:18][C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[N:24]([C:28](=[O:40])[NH:29][C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:39])([F:38])[F:37])[CH:31]=3)[CH:23]=[CH:22]4)=[N:13][CH:12]=[N:11][C:10]=2[CH:9]1[CH3:41])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:39][C:36]([F:37])([F:38])[C:32]1[CH:31]=[C:30]([NH:29][C:28]([N:24]2[C:25]3[C:21](=[CH:20][C:19]([O:18][C:14]4[C:15]5[CH2:16][CH2:17][NH:8][CH:9]([CH3:41])[C:10]=5[N:11]=[CH:12][N:13]=4)=[CH:27][CH:26]=3)[CH:22]=[CH:23]2)=[O:40])[CH:35]=[CH:34][CH:33]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59394655HCID 59394655, compound

Product 1

HCID 59394479HCID 59394479, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution od 8-methyl-4-[1-(3-trifluoromethyl-phenylcarbamoyl)-1H-indol-5-yloxy]-5,8-dihydro-6H-pyrido[3,4-d]pyrimidine-7-carboxylic acid tert-butyl ester (217 mg, 0.38 mmol), DCM (5 mL), and TFA (5 mL) is stirred at rt for 2 h. At that point the solution is concentrated in vacuo and the residue is separated via semi-prep HPLC (C18; 10-100% I/H2O with 0.1% NH4OH) to give the title compound. MS (ESI) m/z 468.1 (M+1); 1H NMR (400 MHz, DMSO-d6) δ ppm 10.39 (s, 1 H), 8.51 (s, 1 H), 8.28 (d, J=9.1 Hz, 1 H), 8.06-8.15 (m, 2 H), 7.97 (d, J=8.6 Hz, 1 H), 7.65 (t, J=8.0 Hz, 1 H), 7.43-7.53 (m, 2 H), 7.13 (dd, J=9.0, 2.4 Hz, 1 H), 6.80 (d, J=3.5 Hz, 1 H), 4.19 (q, J=6.6 Hz, 1 H), 3.34-3.42 (m, 1 H), 3.08-3.20 (m, 1 H), 2.88 (t, J=5.7 Hz, 2 H), 1.49 (d, J=7.1 Hz, 3 H).

Workup

  1. concentrationAt that point the solution is concentrated in vacuo
  2. customthe residue is separated via semi-prep HPLC (C18; 10-100% I/H2O with 0.1% NH4OH)

Sources & evidence

ORD record
ord-09310c9266f9492cbfb08893a728b89a
Source dataset
uspto-grants-2013_09
Patent number
US08541432B2

Reaction notes

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