1,2-Dichloroethane → HCID 24891609, compound

HRID 1880007Notes

Reaction equation

HRID 1880007 reaction equation
C(Cl)CCl.Cl.[CH3:6][C:7]1([CH3:24])[C:13](=[O:14])[NH:12][C:11]2[N:15]=[CH:16][C:17](/[CH:19]=[CH:20]/[C:21]([OH:23])=O)=[CH:18][C:10]=2[CH2:9][O:8]1.C1C=CC2N(O)N=NC=2C=1.[CH3:35][O:36][C:37]1[C:38]([O:47][CH2:48][CH2:49][CH3:50])=[C:39]([C@H:43]([NH:45][CH3:46])[CH3:44])[CH:40]=[CH:41][CH:42]=1.C(N(C(C)C)C(C)C)C>CN(C=O)C.O>[CH3:24][C:7]1([CH3:6])[C:13](=[O:14])[NH:12][C:11]2[N:15]=[CH:16][C:17](/[CH:19]=[CH:20]/[C:21]([N:45]([C@@H:43]([C:39]3[CH:40]=[CH:41][CH:42]=[C:37]([O:36][CH3:35])[C:38]=3[O:47][CH2:48][CH2:49][CH3:50])[CH3:44])[CH3:46])=[O:23])=[CH:18][C:10]=2[CH2:9][O:8]1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 68413051HCID 68413051, compoundHCID 68413716HCID 68413716, compound

Product 1

HCID 24891609HCID 24891609, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
35 °C

Procedure

EDC (0.14 g, 0.73 mmol) was added to a suspension of (E)-3-(3,3-dimethyl-2-oxo-1,2,3,5-tetrahydropyrido[2,3-e][1,4]oxazepin-7-yl)acrylic acid hydrochloride (0.16 g, 0.61 mmol), HOBt (0.091 g, 0.67 mmol), (R)-1-(3-methoxy-2-propoxyphenyl)-N-methylethanamine (0.15 g, 0.67 mmol) and (i-Pr)2EtN (0.62 mL, 3.7 mmol) in DMF (5 mL). The mixture was allowed to stir overnight at 35° C. The mixture was cooled to 0° C. and diluted with H2O (30 mL) with rapid stirring. The resulting precipitate was filtered, washed with H2O (20 mL) then dried under high vacuum. The solid was then triturated with Et2O, and the resultant solid was collected, to yield 125 mg (44%); 1H NMR (300 MHz, DMSO-d6) δ 10.08 (s, 1H), 8.25 (s, 1H), 7.92 and 7.86 (2×s, 1H), 7.47-6.97 (m, 5H), 6.01 and 5.77 (2×s, 1H), 4.07 (s, 2H), 3.83 and 3.73 (2×m, 2H), 3.78 (s, 3H), 2.81 and 2.58 (2×s, 3H), 1.65-1.38 (m, 5H), 1.19 (s, 6H), 0.86 and 0.77 (2×m, 3H); ESI MS m/z 468 [C26H33N3O5+H]+

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with H2O (20 mL)
  4. customthen dried under high vacuum
  5. customThe solid was then triturated with Et2O
  6. customthe resultant solid was collected
  7. customto yield 125 mg (44%)

Sources & evidence

ORD record
ord-3a80256694dd471487e907ec1ce02bc5
Source dataset
uspto-grants-2012_11
Patent number
US08318720B2

Reaction notes

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