Trifluoroacetic acid → HCID 60149002, compound

HRID 1485216Notes

Reaction equation

HRID 1485216 reaction equation
[NH2:1][C:2](=[O:40])[CH2:3][C:4]1[CH:39]=[CH:38][CH:37]=[CH:36][C:5]=1[CH2:6][CH2:7][C:8]1[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][N:11]=[C:10]([NH:18][C:19]2[CH:20]=[C:21]3[C:26](=[CH:27][CH:28]=2)[CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]3)[N:9]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:25]1[C:26]2[C:21](=[CH:20][C:19]([NH:18][C:10]3[N:9]=[C:8]([CH2:7][CH2:6][C:5]4[CH:36]=[CH:37][CH:38]=[CH:39][C:4]=4[CH2:3][C:2]([NH2:1])=[O:40])[C:13]([C:14]([F:16])([F:17])[F:15])=[CH:12][N:11]=3)=[CH:28][CH:27]=2)[CH2:22][CH2:23][NH:24]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71217520HCID 71217520, compound

Product 1

HCID 60149002HCID 60149002, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 6-((4-(2-(2-amino-2-oxoethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)-3,4-dihydroisoquinoline-2(1H)-carboxylate (I82) (136 mg, 0.245 mmol), DCM (10 mL) and TFA (1 mL) were stirred together at room temperature. After three hours the solution was concentrated and the residue treated with 1M sodium hydroxide (25 mL). The resulting suspension was extracted with ethyl acetate (3×50 mL) and the combined organic extracts washed with brine (100 mL), dried and evaporated to give the title compound (21) (81.6 mg, 74% yield) as a white solid; 1H NMR (400 MHz, d6-DMSO) δ 10.06 (s, 1H), 8.65 (s, 1H), 7.51 (s, 1H), 7.48 (dd, J=8.3, 2.1 Hz, 1H), 7.42 (s, 1H), 7.26-7.21 (m, 1H), 7.19-7.13 (m, 3H), 6.96 (d, J=8.3 Hz, 1H), 6.90 (s, 1H), 3.81 (s, 2H), 3.49 (s, 2H), 3.17 (d, J=3.1 Hz, 1H), 3.14-3.06 (m, 2H), 3.05-2.97 (m, 2H), 2.94 (t, J=5.9 Hz, 2H), 2.67 (t, J=5.6 Hz, 2H). LCMS Method C: rt: 4.76 min; m/z 456.1 [M+H]+; m/z 454.1 [M−H]−.

Workup

  1. concentrationAfter three hours the solution was concentrated
  2. additionthe residue treated with 1M sodium hydroxide (25 mL)
  3. extractionThe resulting suspension was extracted with ethyl acetate (3×50 mL)
  4. washthe combined organic extracts washed with brine (100 mL)
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-e3b695a8b2974e5195ffba17d1e15bad
Source dataset
uspto-grants-2016_08
Patent number
US09421205B2

Reaction notes

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