Trifluoroacetic acid → HCID 118006366, compound

HRID 1486798Notes

Reaction equation

HRID 1486798 reaction equation
C(OC(=O)[NH:7][C@@H:8]1[CH2:12][CH2:11][N:10]([CH2:13][C@@H:14]2[O:19][C@H:18]([CH3:20])[CH2:17][N:16]([C:21]3[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[C:27]4[C:22]=3[CH:23]=[CH:24][CH:25]=[N:26]4)[CH2:15]2)[CH2:9]1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][C@@H:8]1[CH2:12][CH2:11][N:10]([CH2:13][C@H:14]2[CH2:15][N:16]([C:21]3[CH:30]=[CH:29][C:28]([C:31]#[N:32])=[C:27]4[C:22]=3[CH:23]=[CH:24][CH:25]=[N:26]4)[CH2:17][C@@H:18]([CH3:20])[O:19]2)[CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 131736818HCID 131736818, compound

Product 1

HCID 118006366HCID 118006366, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl((R)-1-(((2S,6R)-4-(8-cyanoquinolin-5-yl)-6-methylmorpholin-2-yl)methyl)-pyrrolidin-3-yl)carbamate (1.35 g, 3.0 mmol) in DCM (10 mL) was added TFA (8.1 mL). The reaction was stirred at rt after which time it was concentrated and azeotroped to dryness three times with toluene (10 mL each) and then dried under vacuo to provide crude 5-((2S,6R)-2-(((R)-3-aminopyrrolidin-1-yl)methyl)-6-methylmorpholino)quinoline-8-carbonitrile (1.39 g, 3.0 mmol, 100% yield) as the TFA salt.

Workup

  1. concentrationwas concentrated
  2. customazeotroped to dryness three times with toluene (10 mL each)
  3. customdried under vacuo

Sources & evidence

ORD record
ord-f4fe8aad2cf8458a9b8f639e553b48a5
Source dataset
uspto-grants-2016_08
Patent number
US09428495B2

Reaction notes

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