Trifluoroacetic acid → HCID 59599444, compound

HRID 1627559Notes

Reaction equation

HRID 1627559 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:53])[C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:22]=[N:23][C:24]([NH2:52])=[C:25]([O:27][CH:28]([C:30]4[C:35]([Cl:36])=[CH:34][CH:33]=[C:32]([O:37]CC5C(OC)=CC(OC)=CC=5OC)[C:31]=4[Cl:51])[CH3:29])[CH:26]=3)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C>C1(C)C=CC=CC=1>[NH2:52][C:24]1[N:23]=[CH:22][C:21]([C:18]2[CH:17]=[CH:16][C:15]([C:14]([N:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[O:53])=[CH:20][CH:19]=2)=[CH:26][C:25]=1[O:27][CH:28]([C:30]1[C:35]([Cl:36])=[CH:34][CH:33]=[C:32]([OH:37])[C:31]=1[Cl:51])[CH3:29]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 59599433HCID 59599433, compound

Product 1

HCID 59599444HCID 59599444, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 140 mg 4-[4-(6-Amino-5-{1-[2,6-dichloro-3-(2,4,6-trimethoxy-benzyloxy)-phenyl]-ethoxy}-pyridin-3-yl)-benzoyl]-piperazine-1-carboxylic acid tert-butyl ester (from general procedure 53) was added 1 mL TFA, the solution turned reddish immediately followed by addition of 100 μL triethyl silane 3 seconds later. The solution turned to yellow. After stirring for four hours 5 mL of toluene were added and the solvent was removed in vacuo. Chromatography with 10% MeOH/CH2Cl2 to 0.5% to 1% NH4OH/9.5 to 9% MeOH/90% CH2Cl2 led to 55 mg of a white solid, 62° A) yield.

Workup

  1. additionwere added
  2. customthe solvent was removed in vacuo
  3. customled to 55 mg of a white solid, 62°
  4. customyield

Sources & evidence

ORD record
ord-1faf61ab18c94694a52ce6f3191f33b2
Source dataset
uspto-grants-2014_07
Patent number
US08785632B2

Reaction notes

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