Hydrochloric Acid → HCID 46191571, compound

HRID 336878Notes

Reaction equation

HRID 336878 reaction equation
[CH3:1][N:2]1[CH2:25][C:6]2[CH:7]=[N:8][C:9]3[CH:10]=[CH:11][C:12]([C:15]4[CH:16]=[N:17][C:18]5[C:23]([CH:24]=4)=[CH:22][CH:21]=[CH:20][CH:19]=5)=[CH:13][C:14]=3[C:5]=2[N:4]([C:26]2[CH:31]=[CH:30][C:29]([N:32]3[CH2:37][CH2:36][N:35]([C:38]([O:40]C(C)(C)C)=O)[CH2:34][CH2:33]3)=[C:28]([C:45]([F:48])([F:47])[F:46])[CH:27]=2)[C:3]1=[O:49].Cl.CN(C(ON1N=N[C:61]2C=CC=N[C:60]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(O)(=O)CC.CCN(C(C)C)C(C)C>CCO.O1CCOCC1.CN(C=O)C>[CH3:1][N:2]1[CH2:25][C:6]2[CH:7]=[N:8][C:9]3[CH:10]=[CH:11][C:12]([C:15]4[CH:16]=[N:17][C:18]5[C:23]([CH:24]=4)=[CH:22][CH:21]=[CH:20][CH:19]=5)=[CH:13][C:14]=3[C:5]=2[N:4]([C:26]2[CH:31]=[CH:30][C:29]([N:32]3[CH2:37][CH2:36][N:35]([C:38](=[O:40])[CH2:60][CH3:61])[CH2:34][CH2:33]3)=[C:28]([C:45]([F:46])([F:47])[F:48])[CH:27]=2)[C:3]1=[O:49]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 1032Propionic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58524996HCID 58524996, compound

Product 1

HCID 46191571HCID 46191571, compoundYield 17%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 4-(4-(3-methyl-2-oxo-9-(quinolin-3-yl)-3,4-dihydropyrimido[5,4-c]quinolin-1(2H)-yl)-2-(trifluoromethyl)phenyl)piperazine-1-carboxylate (32 mg, 0.047 mmol) in EtOH (1 mL) at room temperature was added a solution of hydrochloric acid in dioxane (4M, 2 mL). The resulting solution was allowed to stir for 4 h. After removal of solvents in vacuo, the residue was redissolved in DMF (2 mL), to which HATU (53 mg, 0.14 mmol), propionic acid (8 μL, 0.094 mmol), and DIEA (24 μL, 0.14 mmol) were added. The resultant solution was stirred for 4 h before filtration. The crude product was subjected to LC-MS-HPLC purification to afford 5 mg of product. LC-MS: (M+H)=9025.22.

Workup

  1. customAfter removal of solvents in vacuo
  2. additionwere added
  3. customThe crude product was subjected to LC-MS-HPLC purification

Sources & evidence

ORD record
ord-70327a85dfee4086b435769e9967d27b
Source dataset
uspto-grants-2014_11
Patent number
US08889706B2

Reaction notes

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