Trifluoroacetic acid → HCID 67891504, compound

HRID 1851638Notes

Reaction equation

HRID 1851638 reaction equation
[F:1][C:2]1[C:7]2[O:8][C:9]3[C:14]([C:15]4([CH2:20][C:19](=[O:21])[N:18]([CH3:22])[C:17]([NH:23]C(=O)OC(C)(C)C)=[N:16]4)[C:6]=2[CH:5]=[C:4]([C:38]2[C:39]([F:44])=[N:40][CH:41]=[CH:42][CH:43]=2)[N:3]=1)=[CH:13][C:12]([C:31]1[C:32]([F:37])=[N:33][CH:34]=[CH:35][CH:36]=1)=[CH:11][CH:10]=3.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:23][C:17]1[N:18]([CH3:22])[C:19](=[O:21])[CH2:20][C:15]2([C:6]3[CH:5]=[C:4]([C:38]4[C:39]([F:44])=[N:40][CH:41]=[CH:42][CH:43]=4)[N:3]=[C:2]([F:1])[C:7]=3[O:8][C:9]3[C:14]2=[CH:13][C:12]([C:31]2[C:32]([F:37])=[N:33][CH:34]=[CH:35][CH:36]=2)=[CH:11][CH:10]=3)[N:16]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86705788HCID 86705788, compound

Product 1

HCID 67891504HCID 67891504, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl 1-fluoro-3,7-bis(2-fluoropyridin-3-yl)-1′-methyl-6′-oxo-5′,6′-dihydro-1′H-spiro[chromeno[2,3-c]pyridine-5,4′-pyrimidine]-2′-ylcarbamate was obtained as a side product in the synthesis of Example 12. To a solution of tert-butyl 1-fluoro-3,7-bis(2-fluoropyridin-3-yl)-1′-methyl-6′-oxo-5′,6′-dihydro-1′H-spiro[chromeno[2,3-c]pyridine-5,4′-pyrimidine]-2′-ylcarbamate (32 mg, 0.053 mmol) in DCM (2.5 mL) was added TFA (500 μL, 6.49 mmol). The reaction was allowed to stir at RT overnight. The reaction mixture was concentrated under reduced pressure, the residue was dissolved in MeOH and loaded onto a Varian Bond Elut SCX column. The column was washed with MeOH and subsequently eluted with a 2 M solution of ammonia in MeOH to obtain 22.6 mg 2′-amino-1-fluoro-3,7-bis(2-fluoropyridin-3-yl)-1′-methyl-1′H-spiro[chromeno[2,3-c]pyridine-5,4′-pyrimidin]-6′(5′H)-one as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in MeOH
  3. washThe column was washed with MeOH
  4. washsubsequently eluted with a 2 M solution of ammonia in MeOH

Sources & evidence

ORD record
ord-359805a33ef247159279cf0b350e0016
Source dataset
uspto-grants-2015_02
Patent number
US08957083B2

Reaction notes

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