Trifluoroacetic acid → HCID 86713612, compound

HRID 2404079Notes

Reaction equation

HRID 2404079 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]2[CH:19]=[CH:18][N:17]=[C:16]([NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[N+:27]([O-:29])=[O:28])[N:15]=2)[CH2:9]1)(C)(C)C.C(O)(C(F)(F)F)=O.NC1CCCN(C2C=CN=C(NC3C=CC=CC=3[N+]([O-])=O)N=2)C1.[CH2:61]([S:64](Cl)(=[O:66])=[O:65])[CH2:62][CH3:63].C(N(CC)CC)C>C(Cl)Cl>[N+:27]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[NH:20][C:16]1[N:15]=[C:14]([N:10]2[CH2:11][CH2:12][CH2:13][CH:8]([NH:7][S:64]([CH2:61][CH2:62][CH3:63])(=[O:66])=[O:65])[CH2:9]2)[CH:19]=[CH:18][N:17]=1)([O-:29])=[O:28]

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 662791-Propanesulfonyl chlorideHCID 86713613HCID 86713613, compoundHCID 86713614HCID 86713614, compound

Product 1

HCID 86713612HCID 86713612, compoundYield 25.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution tert-butyl(1-(2-((2-nitrophenyl)amino)pyrimidin-4-yl)piperidin-3-yl)carbamate (0.14 g, 0.34 mmol) in DCM (2.0 mL) was added TFA (1.0 mL) and the mixture was stirred for 1 h. An aliquot of the reaction mixture was analyzed by LCMS, which indicated that the reaction had proceeded to completion. The solvents were removed and the residue was dried on high vacuum. The crude product was used for the next step without further purification. To a solution of 4-(3-aminopiperidin-1-yl)-N-(2-nitrophenyl)pyrimidin-2-amine (0.34 mmol) in DCM (3.5 mL) at 0° C. was added propane-1-sulfonyl chloride (0.045 mL, 0.4 mmol) and triethylamine (0.12 mL, 0.85 mmol) and the mixture was warmed to room temperature overnight. The crude reaction mixture was concentrated and purified by flash chromatography (0-7.5% MeOH/DCM) to give the title compound (36 mg, 24% yield). MS (ES+) C18H24N6O4S requires: 420. found: 421 [M+H]+.

Workup

  1. customThe solvents were removed
  2. customthe residue was dried on high vacuum
  3. customThe crude product was used for the next step without further purification
  4. customThe crude reaction mixture
  5. concentrationwas concentrated
  6. custompurified by flash chromatography (0-7.5% MeOH/DCM)

Sources & evidence

ORD record
ord-e36c7d9ca7324920a1ca64f73f5ba062
Source dataset
uspto-grants-2014_08
Patent number
US08802697B2

Reaction notes

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