Trifluoroacetic acid → HCID 66970364, compound

HRID 1360336Notes

Reaction equation

HRID 1360336 reaction equation
[CH3:1][N:2]([CH3:29])[C@H:3]1[CH2:7][CH2:6][N:5]([C:8]2[C:13]([C:14]3[O:15][C:16](=[O:28])[C:17]4[C:23]([CH2:24][CH3:25])=[CH:22][C:21]([O:26][CH3:27])=[CH:20][C:18]=4[N:19]=3)=[CH:12][CH:11]=[CH:10][N:9]=2)[CH2:4]1.[F:30][C:31]([F:36])([F:35])[C:32]([OH:34])=[O:33]>C(OCC)C>[F:30][C:31]([F:36])([F:35])[C:32]([OH:34])=[O:33].[CH3:29][N:2]([CH3:1])[C@H:3]1[CH2:7][CH2:6][N:5]([C:8]2[C:13]([C:14]3[O:15][C:16](=[O:28])[C:17]4[C:23]([CH2:24][CH3:25])=[CH:22][C:21]([O:26][CH3:27])=[CH:20][C:18]=4[N:19]=3)=[CH:12][CH:11]=[CH:10][N:9]=2)[CH2:4]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 25205741AX-9657

Product 1

HCID 66970364HCID 66970364, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of compound 132 (120 mg, 0.304 mmol) in diethyl ether (2.0 mL) was added trifluoroacetic acid (0.0215 mL, 0.289 mmol) at room temperature. After stirring for 30 min, the resulting solid was filtered, washed with diethyl ether, and dried in vacuo at room temperature to give 2-[2-((S)-3-Dimethylamino-pyrrolidin-1-yl)-pyridin-3-yl]-5-ethyl-7-methoxy-4H-benz[d][1,3]oxazin-4-one trifluoroacetate (112 mg) as a pale yellow solid. Mp 117-119° C. [α]D25-258 (c 0.56, MeOH). 1H NMR (DMSO-d6, 400 MHz): δ 1.21 (3H, t, J=7.3 Hz), 2.02-2.12 (1H, m), 2.28-2.36 (1H, m), 2.79 (6H, s), 3.08-3.17 (2H, m), 3.47 (1H, dd, J=8.0, 5.5 Hz), 3.67-3.79 (2H, m), 3.86-3.91 (1H, m), 3.91 (3H, s), 6.90 (1H, dd, J=7.9, 4.3 Hz), 7.00 (1H, d, J=2.4 Hz), 7.02 (1H, d, J=2.4 Hz), 8.03 (1H, dd, J=7.4, 1.8 Hz), 8.33 (1H, dd, J=4.3, 1.8 Hz), 9.85 (1H, s). Anal. C, 56.05%; H, 5.21%; N, 10.91%. Calcd for C22H26N4O3.CF3CO2H, C, 56.69%; H, 5.35%; N, 11.02%.

Workup

  1. filtrationthe resulting solid was filtered
  2. washwashed with diethyl ether
  3. customdried in vacuo at room temperature

Sources & evidence

ORD record
ord-2736a3beb4d740cda2e76d7302c852dc
Source dataset
uspto-grants-2011_02
Patent number
US07879846B2

Reaction notes

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