Trifluoroacetic acid → HCID 178419938, compound

HRID 1471013Notes

Reaction equation

HRID 1471013 reaction equation
O=[C:2]([C:30]1[CH:35]=[CH:34][C:33]([C:36]2[NH:40][C:39]([C@@H:41]3[CH2:45][CH2:44][CH2:43][N:42]3C(OC(C)(C)C)=O)=[N:38][CH:37]=2)=[CH:32][CH:31]=1)[CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[NH:17][C:16]([C@@H:18]3[CH2:22][CH2:21][CH2:20][N:19]3C(OC(C)(C)C)=O)=[N:15][CH:14]=2)=[CH:9][CH:8]=1)=O.Cl.Cl.[N:55]1([C:61]2[N:66]=[CH:65][C:64]([NH2:67])=[CH:63][CH:62]=2)[CH2:60][CH2:59][CH2:58][CH2:57][CH2:56]1.C(O)(C(F)(F)F)=O>C1(C)C=CC=CC=1>[NH:19]1[CH2:20][CH2:21][CH2:22][C@H:18]1[C:16]1[NH:15][CH:14]=[C:13]([C:10]2[CH:9]=[CH:8][C:7]([C:5]3[N:67]([C:64]4[CH:63]=[CH:62][C:61]([N:55]5[CH2:56][CH2:57][CH2:58][CH2:59][CH2:60]5)=[N:66][CH:65]=4)[C:2]([C:30]4[CH:35]=[CH:34][C:33]([C:36]5[N:40]=[C:39]([C@@H:41]6[CH2:45][CH2:44][CH2:43][NH:42]6)[NH:38][CH:37]=5)=[CH:32][CH:31]=4)=[CH:3][CH:4]=3)=[CH:12][CH:11]=2)[N:17]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 457923666-(Piperidin-1-yl)pyridin-3-amine dihydrochlorideHCID 59616670di-tert-butyl (2S,2'S)-2,2'-[(1,4-dioxobutane-1,4-diyl)bis(benzene-4,1-diyl-1H-imidazole-5,2-diyl)]dipyrrolidine-1-carboxylate

Product 1

HCID 178419938HCID 178419938, compoundYield 170.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of the product from Example 138B (0.20 g, 0.28 mmol) and the product from Example 144C (0.11 g, 0.42 mmol) in toluene (2.8 mL) was added TFA (22 μL, 0.28 mmol). The mixture was stirred at 110° C. for 3 hours. To the cooled mixture was added TFA (0.5 mL) and the mixture was stirred for 1 h at rt. The solvent was then removed under reduced pressure and triturated with diethylether and dried to provide 0.31 g of the desired compound as a TFA salt. 1HNMR (DMSO-d6; 400 MHz): δ 9.78 (br s, 2H), 7.84 (d, J=2.71 Hz, 1H), 7.75 (s, 2H), 7.67 (AA′XX′, J=8.34 Hz, 4H), 7.35 (dd, J=9.11, 2.71 Hz, 1H), 7.18 (AA′XX′, J=8.46 Hz, 4H), 6.79 (d, J=9.11 Hz, 1H), 6.53 (s, 2H), 4.79 (app t, J=7.81 Hz, 2H), 3.4-3.2 (m, 4H), 2.44-2.36 (m, 2H), 2.25-1.98 (m, 6H), 1.65-1.45 (m, 6H).

Workup

  1. stirringthe mixture was stirred for 1 h at rt
  2. customThe solvent was then removed under reduced pressure
  3. customtriturated with diethylether
  4. customdried

Sources & evidence

ORD record
ord-dd5636cd49d342dd9833fac273215764
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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