Trifluoroacetic acid → HCID 50939341, compound

HRID 1618672Notes

Reaction equation

HRID 1618672 reaction equation
[CH3:1][C:2]1([CH3:44])[C:6]2=[N:7][CH:8]=[C:9]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[CH:10]=[C:5]2[N:4]([C:17]2[C:26]3[C:21](=[CH:22][C:23]([F:28])=[CH:24][C:25]=3[F:27])[N:20]=[C:19]([N:29]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=3)C(=O)OC(C)(C)C)[C:18]=2[CH3:43])[CH2:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][C:2]1([CH3:44])[C:6]2=[N:7][CH:8]=[C:9]([N:11]3[CH2:12][CH2:13][O:14][CH2:15][CH2:16]3)[CH:10]=[C:5]2[N:4]([C:17]2[C:26]3[C:21](=[CH:22][C:23]([F:28])=[CH:24][C:25]=3[F:27])[N:20]=[C:19]([NH:29][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=3)[C:18]=2[CH3:43])[CH2:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67285611HCID 67285611, compound

Product 1

HCID 50939341HCID 50939341, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of tert-butyl 4-(3,3-dimethyl-6-morpholino-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-5,7-difluoro-3-methylquinolin-2-yl(pyridin-2-yl)-carbamate (55.4 mg, 0.092 mmol) in DCM (1 mL) at 0° C. was added TFA (283 μL, 3.68 mmol). The solution was stirred at rt for 30 min, then concentrated and partitioned between EtOAc and saturated aqueous NaHCO3. The organic layer was then dried over MgSO4 and concentrated under reduced pressure to give 4-(3,3-dimethyl-6-morpholino-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-5,7-difluoro-3-methyl-N-(pyridin-2-yl)quinolin-2-amine as a rust-colored solid. 1H NMR (400 MHz, chloroform-d) δ ppm 8.85 (1H, d, J=8.4 Hz), 8.31-8.35 (1H, m), 7.78-7.85 (1H, m), 7.58 (1H, br. s.), 7.54 (1H, d, J=2.3 Hz), 7.39-7.45 (1H, m), 7.01-7.08 (1H, m), 6.73-6.80 (1H, m), 5.68-5.71 (1H, m), 3.81-3.86 (1H, m), 3.72-3.79 (4H, m), 3.58-3.63 (1H, m), 2.97-3.04 (4H, m), 2.34 (3H, s), 1.53 (3H, s), 1.50 (3H, s). Mass Spectrum (ESI) m/e=503.2 (M+1).

Workup

  1. concentrationconcentrated
  2. custompartitioned between EtOAc and saturated aqueous NaHCO3
  3. dry with materialThe organic layer was then dried over MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c681d04df31e4092813ded66c5604d11
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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