1,2-Dichloroethane → HCID 66670722, compound

HRID 1517853Notes

Reaction equation

HRID 1517853 reaction equation
[OH:1][C@H:2]([CH3:39])[CH2:3][N:4]1[C:8]([CH3:9])=[C:7]([C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]3[C:29]4[C:24](=[CH:25][C:26]([O:30][CH3:31])=[CH:27][CH:28]=4)[N:23]=[CH:22][CH:21]=3)=[CH:15][N:14]=2)=[O:11])[C:6](=[O:32])[N:5]1[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[C:40]([N:50]([CH2:52][C:53](O)=[O:54])[CH3:51])([O:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)=[O:41].C(Cl)CCl>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:43]([O:42][C:40]([N:50]([CH3:51])[CH2:52][C:53]([O:1][C@H:2]([CH3:39])[CH2:3][N:4]1[C:8]([CH3:9])=[C:7]([C:10](=[O:11])[NH:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]3[C:29]4[C:24](=[CH:25][C:26]([O:30][CH3:31])=[CH:27][CH:28]=4)[N:23]=[CH:22][CH:21]=3)=[CH:15][N:14]=2)[C:6](=[O:32])[N:5]1[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)=[O:54])=[O:41])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 97053N-CarbobenzoxysarcosineHCID 59598374HCID 59598374, compound

Product 1

HCID 66670722HCID 66670722, compoundYield 77.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a mixture of (R)-1-(2-hydroxypropyl)-N-(5-(7-methoxyquinolin-4-yloxy)pyridin-2-yl)-5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide (2.0 g, 3.81 mmol), N-Cbz-sarcosine (1.7 g, 7.62 mmol) and DMAP (0.93 g, 7.62 mmol, Aladdin) in 15 mL of CH2Cl2 at 0° C. was added EDC solid (2.19 g, 11.43 mmol, Aladdin) in portions. After stirring at 0° C. for 2 hrs, the mixture was allowed to heat to 40° C. and stirred overnight. The reaction was diluted with 100 mL of CH2Cl2. The resulted solution was washed with 0.1 N HCl (10 mL×2), saturated NaHCO3 (20 mL×2) and followed by water (20 mL). The organic phase was dried over Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (EtOAc/MeOH=4/1) to give the title compound as a yellow solid (2.15 g, 77.3%).

Workup

  1. temperatureto heat to 40° C.
  2. stirringstirred overnight
  3. washThe resulted solution was washed with 0.1 N HCl (10 mL×2), saturated NaHCO3 (20 mL×2)
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by a silica gel column chromatography (EtOAc/MeOH=4/1)

Sources & evidence

ORD record
ord-405d925084324e649c11542c4260eca0
Source dataset
uspto-grants-2012_07
Patent number
US08232294B2

Reaction notes

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