Trifluoroacetic acid → HCID 178425092, compound

HRID 1848874Notes

Reaction equation

HRID 1848874 reaction equation
C([O:8][C:9]1[N:14]=[CH:13][C:12]([O:15][C:16]2[CH:44]=[C:43]([N:45]3[CH2:50][CH2:49][N:48]([CH2:51][C:52]4[CH2:57][CH2:56][C:55]([CH3:59])([CH3:58])[CH2:54][C:53]=4[C:60]4[CH:65]=[CH:64][C:63]([Cl:66])=[CH:62][CH:61]=4)[CH2:47][CH2:46]3)[CH:42]=[CH:41][C:17]=2[C:18]([NH:20][S:21]([C:24]2[CH:29]=[CH:28][C:27]([NH:30][CH2:31][CH:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)=[C:26]([N+:38]([O-:40])=[O:39])[CH:25]=2)(=[O:23])=[O:22])=[O:19])=[CH:11][CH:10]=1)C1C=CC=CC=1.FC(F)(F)C(O)=O>ClCCl>[Cl:66][C:63]1[CH:62]=[CH:61][C:60]([C:53]2[CH2:54][C:55]([CH3:58])([CH3:59])[CH2:56][CH2:57][C:52]=2[CH2:51][N:48]2[CH2:47][CH2:46][N:45]([C:43]3[CH:42]=[CH:41][C:17]([C:18]([NH:20][S:21]([C:24]4[CH:29]=[CH:28][C:27]([NH:30][CH2:31][CH:32]5[CH2:37][CH2:36][O:35][CH2:34][CH2:33]5)=[C:26]([N+:38]([O-:40])=[O:39])[CH:25]=4)(=[O:23])=[O:22])=[O:19])=[C:16]([O:15][C:12]4[CH:13]=[N:14][C:9]([OH:8])=[CH:10][CH:11]=4)[CH:44]=3)[CH2:50][CH2:49]2)=[CH:65][CH:64]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86642875HCID 86642875, compound

Product 1

HCID 178425092HCID 178425092, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
40 °C

Procedure

To 2-(6-(benzyloxy)pyridin-3-yloxy)-4-(4-((2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl)methyl)piperazin-1-yl)-N-(3-nitro-4-((tetrahydro-2H-pyran-4-yl)methylamino)phenylsulfonyl)benzamide (0.132 g) in dichloromethane (1 mL) was added trifluoroacetic acid (0.33 mL) and the reaction was sealed in a vial under nitrogen and heated to 40° C. After stirring for 16 hours, the reaction was cooled, diluted with dichloromethane (50 mL) and washed with sodium carbonate (2×25 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography (GraceResolv 12 g) eluting with a gradient of 0.3% to 3% methanol/dichloromethane (Flow=36 mL/minute) over 30 minutes gave the title compound. 1H NMR (300 MHz, CDCl3) δ 12.51-11.38 (m, 1H), 9.78 (s, 1H), 8.89 (d, 1H), 8.52 (t, 1H), 8.19 (dd, 1H), 7.92 (d, 1H), 7.43-7.33 (m, 2H), 7.24 (d, 2H), 7.00-6.89 (m, 3H), 6.74-6.67 (m, 1H), 6.55 (dd, 1H), 6.00 (d, 1H), 4.00 (d, 2H), 3.42 (dd, 2H), 3.34-3.23 (m, 2H), 3.16 (s, 4H), 2.79 (s, 2H), 2.24 (d, 6H), 1.99 (s, 3H), 1.72 (s, 2H), 1.55-1.33 (m, 4H), 0.96 (s, 6H).

Workup

  1. customthe reaction was sealed in a vial under nitrogen
  2. temperaturethe reaction was cooled
  3. washwashed with sodium carbonate (2×25 mL)
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washSilica gel chromatography (GraceResolv 12 g) eluting with a gradient of 0.3% to 3% methanol/dichloromethane (Flow=36 mL/minute) over 30 minutes

Sources & evidence

ORD record
ord-e415a042e53c4a65af2b781fcb588168
Source dataset
uspto-grants-2015_02
Patent number
US08952157B2

Reaction notes

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