Trifluoroacetic acid → HCID 59730297, compound

HRID 228167Notes

Reaction equation

HRID 228167 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][CH2:15][C:16]([C:19]1[CH:24]=[CH:23][C:22]([O:25][C:26]2[CH:31]=[CH:30][C:29]([C:32](=[O:34])[NH2:33])=[CH:28][N:27]=2)=[CH:21][CH:20]=1)([CH3:18])[CH3:17])(C)(C)C>ClCCl>[NH2:14][CH2:15][C:16]([C:19]1[CH:20]=[CH:21][C:22]([O:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]([NH2:33])=[O:34])=[CH:28][N:27]=2)=[CH:23][CH:24]=1)([CH3:18])[CH3:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59730164HCID 59730164, compound

Product 1

HCID 59730297HCID 59730297, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add trifluoroacetic acid (2.0 mL, 26.0 mmol) to a stirred solution of {2-[4-(5-carbamoyl-pyridin-2-yloxy)-phenyl]-2-methyl-propyl}-carbamic acid tert-butyl ester (0.5000 g, 1.297 mmol) in dichloromethane (8 mL). Stir the reaction at room temperature under nitrogen for 2.5 h. Load the reaction contents directly onto a 10 g prepacked SCX cartridge, flush with methanol (200 mL), and elute the product with 2 M ammonia in methanol (75 mL). Concentrate the eluant on a rotary evaporator to give the crude product. The crude product is purified by flash chromatography on silica gel eluting with 1.5% concentrated ammonium hydroxide/15% ethanol/chloroform to yield 0.2626 g (71%) of 6-[4-(2-amino-1,1-dimethyl-ethyl)-phenoxy]-nicotinamide: mass spectrum (ion spray): m/z=286.1 (M+1); 1H NMR (DMSO-d6): 8.59 (d, 1H), 8.23 (dd, 1H), 8.01 (s, 1H), 7.46 (s, 1H), 7.40-7.36 (m, 2H), 7.08-7.02 (m, 3H), 3.32 (br s, 2H), 2.64 (s, 2H), 1.22 (s, 6H).

Workup

  1. customthe reaction at room temperature under nitrogen for 2.5 h
  2. customLoad the reaction contents directly onto a 10 g prepacked SCX cartridge
  3. customflush with methanol (200 mL)
  4. washelute the product with 2 M ammonia in methanol (75 mL)
  5. concentrationConcentrate the eluant
  6. customon a rotary evaporator
  7. customto give the crude product
  8. customThe crude product is purified by flash chromatography on silica gel eluting with 1.5% concentrated ammonium hydroxide/15% ethanol/chloroform

Sources & evidence

ORD record
ord-2f223a3cfc6d4ab1a90a1b9d6d5558dc
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Reaction notes

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