Trifluoroacetic acid → HCID 86713606, compound

HRID 2404071Notes

Reaction equation

HRID 2404071 reaction equation
[CH3:1][C:2]1[C:3]([N:28]2[CH2:33][CH2:32][N:31]([C:34]([O:36]C(C)(C)C)=O)[CH2:30][CH2:29]2)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:24])[NH:16][CH:17]3[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]3)=[CH:11][C:10]=2[N+:25]([O-:27])=[O:26])=[N:6][CH:7]=1.C(O)(C(F)(F)F)=O.CC1C(N2CCNCC2)=NC([NH:55][C:56]2[CH:71]=[CH:70][C:59]([C:60]([NH:62]C3CCN(C)CC3)=O)=[CH:58][C:57]=2[N+]([O-])=O)=NC=1.N(C1C=CC(C#N)=CC=1)=C=O.C(N(CC)CC)C>C(Cl)Cl>[C:60]([C:59]1[CH:70]=[CH:71][C:56]([NH:55][C:34]([N:31]2[CH2:32][CH2:33][N:28]([C:3]3[C:2]([CH3:1])=[CH:7][N:6]=[C:5]([NH:8][C:9]4[CH:14]=[CH:13][C:12]([C:15](=[O:24])[NH:16][CH:17]5[CH2:18][CH2:19][N:20]([CH3:23])[CH2:21][CH2:22]5)=[CH:11][C:10]=4[N+:25]([O-:27])=[O:26])[N:4]=3)[CH2:29][CH2:30]2)=[O:36])=[CH:57][CH:58]=1)#[N:62]

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 1703804-Cyanophenyl isocyanateHCID 86713605HCID 86713605, compoundHCID 86713607HCID 86713607, compound

Product 1

HCID 86713606HCID 86713606, compoundYield 222%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl 4-(5-methyl-2-((4-((1-methylpiperidin-4-yl)carbamoyl)-2-nitrophenyl)amino)pyrimidin-4-yl)piperazine-1-carboxylate (0.073 g, 0.13 mmol) in DCM (1.0 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-((5-methyl-4-(piperazin-1-yl)pyrimidin-2-yl)amino)-N-(1-methylpiperidin-4-yl)-3-nitrobenzamide (0.073 mmol) in DCM (1.5 mL) was added 4-isocyanatobenzonitrile (23 mg, 0.16 mmol) and triethylamine (0.055 mL, 0.39 mmol) and the mixture was stirred at 23° C. for 16 h. reaction. The crude reaction mixture was filtered and washed with minimal volume of DCM and then hexanes to give the title compound (97 mg, 100%). MS (ES+) C30H34N10O4 requires: 598. found: 599 [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. stirringthe mixture was stirred at 23° C. for 16 h.
  5. customreaction
  6. customThe crude reaction mixture
  7. filtrationwas filtered
  8. washwashed with minimal volume of DCM

Sources & evidence

ORD record
ord-6a1b4aad145545d187ff8f557fb71df4
Source dataset
uspto-grants-2014_08
Patent number
US08802697B2

Reaction notes

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