Trifluoroacetic acid → HCID 178426864, compound

HRID 929104Notes

Reaction equation

HRID 929104 reaction equation
C(O)(C(F)(F)F)=O.[CH3:8][C:9]1[CH:46]=[C:45]([CH3:47])[CH:44]=[CH:43][C:10]=1[O:11][CH2:12][C@H:13]([OH:42])[CH2:14][NH:15][C:16]1[CH:21]=[CH:20][NH:19][C:18](=[O:22])[C:17]=1[C:23]1[NH:34][C:33]2[C:25](=[CH:26][C:27]3[CH2:28][N:29]([CH:36]4[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]4)[C:30](=[O:35])[C:31]=3[CH:32]=2)[N:24]=1.[CH:48]([S:50]([CH3:53])(=[O:52])=[O:51])=[CH2:49]>CCO>[CH3:8][C:9]1[CH:46]=[C:45]([CH3:47])[CH:44]=[CH:43][C:10]=1[O:11][CH2:12][C@H:13]([OH:42])[CH2:14][NH:15][C:16]1[CH:21]=[CH:20][NH:19][C:18](=[O:22])[C:17]=1[C:23]1[NH:34][C:33]2[C:25](=[CH:26][C:27]3[CH2:28][N:29]([CH:36]4[CH2:37][CH2:38][N:39]([CH2:49][CH2:48][S:50]([CH3:53])(=[O:52])=[O:51])[CH2:40][CH2:41]4)[C:30](=[O:35])[C:31]=3[CH:32]=2)[N:24]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 19354Methyl vinyl sulfoneHCID 1784268602-(4-[(R)-3-(2,4-dimethyl-phenoxy)-2-hydroxy-propylamino]-2-oxo-1,2-dihydro-pyridin-3-yl)-6-piperidin-4-yl-6,7-dihydro-3H-1,3,6-triaza-s-indacen-5-one

Product 1

HCID 178426864HCID 178426864, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of the TFA salt of 2-{4-[(R)-3-(2,4-dimethyl-phenoxy)-2-hydroxy-propylamino]-2-oxo-1,2-dihydro-pyridin-3-yl}-6-piperidin-4-yl-6,7-dihydro-3H-1,3,6-triaza-s-indacen-5-one (40 mg, 0.061 mmol) and methyl vinyl sulfone (318.4 mg, 3.0 mmol) in EtOH (2.0 mL) was heated at 90° C. for 22 h and then evaporated. Chromatography of the residue with CH2Cl2/MeOH/28% aqueous NH4OH (125:10:1) afforded a fluorescent product which was subjected to HPLC purification to afford the title compound in TFA salt form. 1H NMR (DMSO-d6) δ 2.01-2.17 (4H), 2.19 (s, 3H, CH3), 2.21 (s, 3H, CH3), 3.15 (s, 3H, CH3), 3.23 (m, 2H), 3.51-3.75 (8H), 4.01 (m, 2H), 4.15 (m, 1H), 4.34 (m, 1H), 4.47 (s, 2H), 6.22 (d, J=7 Hz, 1H), 6.84 (d, J=7 Hz, 1H), 6.94 (d, J=7 Hz, 1H), 6.98 (s, 1H), 7.36 (dd, J=7 Hz and 6 Hz, 1H), 7.59 (br s, 1H), 7.83 (br s, 1H), 11.14 (br s, 1H, NH), 11.23 (br d, J=6 Hz, 1H, NH); ESI-MS m/z 649.5 (MH+).

Workup

  1. customevaporated
  2. customChromatography of the residue with CH2Cl2/MeOH/28% aqueous NH4OH (125:10:1) afforded a fluorescent product which
  3. customwas subjected to HPLC purification

Sources & evidence

ORD record
ord-28d751d7d22344e68a7f25b31efce9c4
Source dataset
uspto-grants-2016_03
Patent number
US09290503B2

Reaction notes

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