Acetic Anhydride → HCID 11224536, compound

HRID 1866909Notes

Reaction equation

[Cl:1][C:2]1[C:3](=[O:28])[N:4]([CH2:18][C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[NH:24][CH:23]=[CH:22]3)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[F:17].[C:29](OC(=O)C)(=[O:31])[CH3:30].CCN(CC)CC>CC#N>[C:29]([N:24]1[C:25]2[C:21](=[CH:20][C:19]([CH2:18][N:4]3[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]4[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=4[F:17])=[C:2]([Cl:1])[C:3]3=[O:28])=[CH:27][CH:26]=2)[CH:22]=[CH:23]1)(=[O:31])[CH3:30]

Participants

Conditions

Temperature: 86 °C

Procedure

To a solution of 3-chloro-4-(2,4-difluorobenzyloxy)-1-(1H-indol-5-ylmethyl)-1H-pyridin-2-one (Step 5, synthesis of Example 86) (0.22 g, 0.57 mmol) in CH3CN (10 mL) was added acetic anhydride (0.06 mL, 0.58 mmol) and Et3N (2 mL), and the reaction mixture was stirred at 86° C. for 6 h. The reaction mixture was cooled to room temperature, and partitioned between 1 N HCl and EtOAc. The organic solution was separated, washed with brine, dried (Na2SO4), filtered, and concentrated under reduced pressure. 1H NMR (300 MHz, MeOD) δ 8.35 (d, J=9 Hz, 1H), 7.77 (d, J=9 Hz, 1H), 7.70 (d, J=3 Hz, 1H), 7.54 (s, 2H), 7.31 (d, J=9 Hz, 1H), 7.01-6.99 (m, 2H), 6.66 (d, J=3 Hz, 1H), 6.59 (d, J=9 Hz, 1H), 5.29 (s, 4H), 2.63 (s, 3H). ESHRMS m/z 443.0965 (M+H C23H18ClF2N2O3 requires 443.0969).

Workup

temperatureThe reaction mixture was cooled to room temperature
custompartitioned between 1 N HCl and EtOAc
customThe organic solution was separated
washwashed with brine
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-5190ea47ede344729c8e0704c08779b1
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07629363B2

Reaction notes

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