Trifluoroacetic acid → HCID 67966906, compound

HRID 527591Notes

Reaction equation

HRID 527591 reaction equation
C(O)(C(F)(F)F)=O.CC([N:12]([C:16]([CH3:39])([CH3:38])[C:17]([NH:19][C:20]1[CH:21]=[N:22][C:23]([O:26][C:27]2[CH:36]=[CH:35][CH:34]=[C:33]3[C:28]=2[CH2:29][CH:30]([CH3:37])[CH2:31][O:32]3)=[CH:24][CH:25]=1)=[O:18])C(=O)[O-])(C)C>ClCCl>[CH3:39][C:16]([C:17]([NH:19][C:20]1[CH:21]=[N:22][C:23]([O:26][C:27]2[CH:36]=[CH:35][CH:34]=[C:33]3[C:28]=2[CH2:29][CH:30]([CH3:37])[CH2:31][O:32]3)=[CH:24][CH:25]=1)=[O:18])([CH3:38])[NH2:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86698435HCID 86698435, compound2×

Product 1

HCID 67966906HCID 67966906, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In a 50 ml round-bottomed flask 1,1-dimethylethyl[1,1-dimethyl-2-({6-[(3-methyl-3,4-dihydro-2H-chromen-5-yl)oxy]-3-pyridinyl}amino)-2-oxoethyl]carbamate (Intermediate 120, 104.0 mg) was dissolved in dichloromethane (6 ml) to give a pale yellow solution. The reaction mixture was cooled at 0° C. and TFA (2 ml, 26.0 mmol) was added. The reaction mixture was stirred at 0° C. After 2 h 30 min, the mixture was evaporated under vacuum to give the crude product which was charged on a 5 g SCX cartridge. It was then flushed with 40 ml of methanol followed by 40 ml of a 2M solution of ammonia in methanol. The ammonia eluate was evaporated under vacuum to give the title compound as a colourless oil (72.6 mg).

Workup

  1. customto give a pale yellow solution
  2. customthe mixture was evaporated under vacuum
  3. customto give the crude product which
  4. additionwas charged on a 5 g SCX cartridge
  5. customIt was then flushed with 40 ml of methanol
  6. customThe ammonia eluate was evaporated under vacuum

Sources & evidence

ORD record
ord-2d45c831b918486794622fb3e502e683
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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