Trifluoroacetic acid → HCID 24960733, compound

HRID 1662830Notes

Reaction equation

HRID 1662830 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:20])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)=[CH:7][C:3]=1[C:4]([OH:6])=O.ClC1N=C(OC)N=C(OC)N=1.CN1CCOCC1.C(OC([N:46]1[CH2:51][CH2:50][CH:49]([S:52]([C:55]2[CH:60]=[CH:59][C:58]([NH:61][C:62]3[N:67]=[CH:66][C:65]([NH2:68])=[CH:64][N:63]=3)=[CH:57][CH:56]=2)(=[O:54])=[O:53])[CH2:48][CH2:47]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:20])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)=[CH:7][C:3]=1[C:4]([NH:68][C:65]1[CH:66]=[N:67][C:62]([NH:61][C:58]2[CH:59]=[CH:60][C:55]([S:52]([CH:49]3[CH2:50][CH2:51][NH:46][CH2:47][CH2:48]3)(=[O:53])=[O:54])=[CH:56][CH:57]=2)=[N:63][CH:64]=1)=[O:6]

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 79724-MethylmorpholineHCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 28667434HCID 28667434, compoundHCID 587487264-(4-(5-Amino-pyrimidin-2-ylamino)-benzenesulfonyl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 24960733HCID 24960733, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Intermediate 19 (Example 27) (0.136 g, 0.44 mmol) was combined with 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) (0.093 g, 0.53 mmol) and diluted with DCM (4 mL). This was immediately treated with 4-methyl morpholine (0.10 mL, 0.88 mmol) and allowed to stir at ambient temperature for 1 h. Intermediate 13 (Example 20) (0.20 g, 0.462 mmol) was then added in one portion. Stirring was continued overnight. After 18 h, reaction solvents were removed and resulting crude solids were diluted with DCM (4 mL) and treated with TFA (0.2 mL). After 2 h, reaction solvents were removed and resulting crude solids purified via HPLC to afford the title compound as a white solid (0.030 g, 11%).

Workup

  1. stirringStirring
  2. waitwas continued overnight
  3. waitAfter 18 h
  4. customreaction solvents
  5. customwere removed
  6. customresulting crude solids
  7. waitAfter 2 h
  8. customreaction solvents
  9. customwere removed
  10. customresulting crude solids
  11. custompurified via HPLC

Sources & evidence

ORD record
ord-3ae72a55c64048bf9cc57e79b876d18b
Source dataset
uspto-grants-2011_10
Patent number
US08030487B2

Reaction notes

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