Triethylamine → HCID 86683602, compound

HRID 1509198Notes

Reaction equation

C(OC(=O)[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:23]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:22][C:21]([N+:30]([O-])=O)=[C:20](Cl)[N:19]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)(C)(C)C.Cl.[CH3:36][NH:37][CH2:38][C:39](OC)=[O:40].C(N(CC)CC)C>CO>[NH2:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:23]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)=[CH:22][C:21]4[NH:30][C:39](=[O:40])[CH2:38][N:37]([CH3:36])[C:20]=4[N:19]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1

Participants

Conditions

Temperature: 80 °C

Procedure

In a microwave vial were added tert-butyl(1-(4-(6-chloro-5-nitro-3-phenylpyridin-2-yl)phenyl)cyclobutyl)carbamate (200 mg, 0.417 mmol), methyl 2-(methylamino)acetate hydrochloride (58 mg, 0.417 mmol) and triethylamine (58 μl, 0.417 mmol) in methanol (2 ml). The solution was heated to 80° C. under microwave irradiation for 1 hour. The reaction mixture was concentrated to dryness under reduced pressure and purified by Biotage chromatography (cyclohexane:ethyl acetate, gradient elution from 100:0 to 0:100) to afford the title compound (103 mg, 65%). 1H NMR (500 MHz, CDCl3): 8.29 (1H, s), 7.25-7.38 (7H, m), 7.15-7.23 (2H, m), 5.05 (1H, br s), 4.39 (2H, s), 3.83 (3H, s), 3.11 (3H, s), 2.25-2.65 (4H, m), 2.05-2.20 (1H, m), 1.80-1.95 (1H, m), 1.10-1.50 (9H, br).

Workup

concentrationThe reaction mixture was concentrated to dryness under reduced pressure
custompurified by Biotage chromatography (cyclohexane:ethyl acetate, gradient elution from 100:0 to 0:100)

Sources & evidence

ORD record: ord-0b81fbf1b26f489ca40ef8fa201a4974
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221838B2

Reaction notes

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