Acetyl chloride → HCID 49869916, compound

HRID 474942Notes

Reaction equation

[C:1](Cl)([CH3:3])=[O:2].Cl.[CH2:6]([O:13][C:14]1[CH:19]=[CH:18][N:17]([C:20]2[CH:21]=[CH:22][C:23]3[C:24]4[CH2:33][CH2:32][NH:31][CH2:30][CH2:29][C:25]=4[NH:26][C:27]=3[CH:28]=2)[C:16](=[O:34])[CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CCN(CC)CC>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:1]([N:31]1[CH2:32][CH2:33][C:24]2[C:23]3[CH:22]=[CH:21][C:20]([N:17]4[CH:18]=[CH:19][C:14]([O:13][CH2:6][C:7]5[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=5)=[CH:15][C:16]4=[O:34])=[CH:28][C:27]=3[NH:26][C:25]=2[CH2:29][CH2:30]1)(=[O:2])[CH3:3]

Participants

Conditions

Temperature: 25 °C

Procedure

AcCl (0.03 mL, 0.4 mmol) was added to a solution of 4-(benzyloxy)-1-(1,2,3,4,5,6-hexahydroazepino[4,5-b]indol-8-yl)pyridin-2(1H)-one hydrochloride (102 mg, 0.242 mmol), DMAP (6 mg, 0.05 mmol) and Et3N (0.10 mL, 0.73 mmol) in CH2Cl2 (10 mL) under N2, and the resulting solution was stirred at 25° C. for 4 h. The solution was concentrated under reduced pressure. Flash chromatography on silica gel (Et2O/(8:1.9:0.1 Et2O/MeOH/NH4OH) afforded 35 mg (34%) of the title compound as an off-white solid: mp 250-254° C.; 1H NMR (500 MHz, DMSO-d6) δ 10.99 (s, 1H), 7.54 (d, J=7.5 Hz, 1H), 7.49-7.35 (m, 6H), 7.19 (dd, J=2.5, 2.5 Hz, 1H), 6.88-6.83 (m, 1H), 6.07 (dd, J=8.0, 2.5 Hz, 1H), 5.95 (d, J=2.5, 1H), 5.14 (s, 2H), 3.76-3.65 (m, 4H), 3.06-3.02 (m, 1H), 2.97-2.91 (m, 2H), 2.87-2.82 (m, 1H), 2.12 (s, 3H); ESI MS m/z 428 [M+H]+.

Workup

concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record: ord-7d6b48e166f0458f90bef9418789f018
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637501B2

Reaction notes

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