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HCID 43600040, compound → HCID 90331390, compound

HRID 2284897
Notes
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Reaction equation

HRID 2284897 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 43600040HCID 43600040, compoundHCID 86729633HCID 86729633, compoundHCID 131733538HCID 131733538, compound

Product 1

HCID 90331390HCID 90331390, compound

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

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

  1. concentrationthe reaction mixture was concentrated
  2. additiondiluted with water (30 mL)
  3. filtrationthe precipitate was filtered
  4. washwashed with saturated sodium bicarbonate solution (15 ml)
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes