Trifluoroacetic acid → HCID 66587534, compound

HRID 625370Notes

Reaction equation

HRID 625370 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([C:16]3[N:21]=[C:20]([CH2:22][N:23]4[CH2:29][CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24]4)[CH:19]=[CH:18][CH:17]=3)=[O:15])=[C:9]([C:37]3[CH:42]=[C:41]([C:43](=[O:56])[NH:44][CH2:45][C:46]4[CH:51]=[CH:50][CH:49]=[C:48]([C:52]([F:55])([F:54])[F:53])[CH:47]=4)[CH:40]=[CH:39][N:38]=3)[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[N:23]1([CH2:22][C:20]2[N:21]=[C:16]([C:14]([NH:13][C:10]3[CH:11]=[CH:12][C:7]([N:1]4[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]4)=[CH:8][C:9]=3[C:37]3[CH:42]=[C:41]([C:43](=[O:56])[NH:44][CH2:45][C:46]4[CH:51]=[CH:50][CH:49]=[C:48]([C:52]([F:53])([F:55])[F:54])[CH:47]=4)[CH:40]=[CH:39][N:38]=3)=[O:15])[CH:17]=[CH:18][CH:19]=2)[CH2:29][CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 66588078HCID 66588078, compound

Product 1

HCID 66587534HCID 66587534, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Into a 50-mL round-bottom flask, was placed a solution of tert-butyl 4-((6-(4-(piperidin-1-yl)-2-(4-(3-(trifluoromethyl)benzylcarbamoyl)pyridin-2-yl)phenylcarbamoyl)pyridin-2-yl)methyl)-1,4-diazepane-1-carboxylate (150 mg, 0.18 mmol, 1.00 equiv, 95%) in dichloromethane (5 mL), and trifluoroacetic acid (1 mL). The resulting solution was stirred overnight at room temperature. The resulting solution was diluted with 50 mL of dichloromethane. The solution was adjusted to pH 9 with aqueous sodium bicarbonate. The resulting solution was extracted with 3×50 mL of dichloromethane and the organic layers combined, dried over anhydrous sodium sulfate, and concentrated under vacuum. The product was obtained as 120 mg (97%) of a yellow solid.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. extractionThe resulting solution was extracted with 3×50 mL of dichloromethane
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-1ed697f2135c49959fceb6700820b63c
Source dataset
uspto-grants-2016_04
Patent number
US09301951B2

Reaction notes

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