HCID 43600040, compound → HCID 90331390, compound

HRID 2284897Notes

Reaction equation

[Cl:1][C:2]1[C:3](S(C)=O)=[N:4][C:5]([NH:8][C@@H:9]2[CH2:14][CH2:13][CH2:12][C@H:11]([C:15]([NH2:17])=[O:16])[CH2:10]2)=[N:6][CH:7]=1.CC1C=CC(S(O)(=O)=O)=CC=1.O1CCOCC1.[NH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[NH:45][C:46](=[O:49])[CH:47]=[CH2:48]>CO.C(Cl)(Cl)Cl>[C:46]([NH:45][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=1[NH:38][C:3]1[C:2]([Cl:1])=[CH:7][N:6]=[C:5]([NH:8][C@@H:9]2[CH2:14][CH2:13][CH2:12][C@H:11]([C:15]([NH2:17])=[O:16])[CH2:10]2)[N:4]=1)(=[O:49])[CH:47]=[CH2:48]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of Intermediate 3 (1.4 g, 4.43 mmol) in 0.04 M PTSA/1,4-dioxane (12 mL, 0.106 mmol) was added N-(2-aminophenyl)acrylamide (1.72 g, 6.64 mmol), and the reaction mixture was stirred at 70° C. for 1 h. After completion of the reaction (TLC System: 5% methanol/chloroform, (Rf): 0.5), the reaction mixture was concentrated and diluted with water (30 mL), and the precipitate was filtered, washed with saturated sodium bicarbonate solution (15 ml) and dried to afford the desired compound as a white solid. (1.1 g, 59.7%). 1H NMR (400 MHz, DMSO-d6) δ 1.21-1.26 (m, 3H), 1.26-1.32 (m, 2H), 1.67-1.69 (m, 2H), 1.76-1.79 (m, 2H), 2.05 (m, 1H), 5.79 (d, 1H J=11.4 Hz), 6.28-6.32 (d, 1H J=16.9 Hz), 6.46-6.52 (dd, 1H J=10.2 Hz and 17 Hz), 6.64 (br s, 1H), 7.14 (br s, 1H), 7.22-7.27 (m, 2H), 7.43 (d, 1H J=7.4 Hz), 7.74 (d, 1H J=7.8 Hz), 8.01 (s, 1H), 8.86 (br s, 1H), 10.15 (s, 1H). MS m/z: 415.2 (ES+, M+H).

Workup

concentrationthe reaction mixture was concentrated
additiondiluted with water (30 mL)
filtrationthe precipitate was filtered
washwashed with saturated sodium bicarbonate solution (15 ml)
customdried

Sources & evidence

ORD record: ord-f4d26582e82c448b8d96ad1b01781487
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145387B2

Reaction notes

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