Hydrazine hydrate (1:1) → HCID 68600217, compound

HRID 1185533Notes

Reaction equation

HRID 1185533 reaction equation
C([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:49])[C@@H:13]([NH:19][C:20]([C:22]2[CH:31]=[C:30]([O:32][CH2:33][C:34]([N:36]3[CH2:40][CH2:39][CH2:38][C@H:37]3[C:41](=[O:47])[NH:42][CH:43]3[CH2:46][CH2:45][CH2:44]3)=[O:35])[C:29]3[C:24](=[CH:25][C:26]([CH3:48])=[CH:27][CH:28]=3)[N:23]=2)=[O:21])[CH2:14][CH2:15][C:16](O)=[O:17])[CH2:8][CH2:7]1)=O)C.[B-](F)(F)(F)F.[CH3:55][CH2:56]OC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.[OH2:72].[NH2:73][NH2:74]>C(Cl)Cl.O>[CH2:55]([O:72][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:49])[C@@H:13]([NH:19][C:20]([C:22]2[CH:31]=[C:30]([O:32][CH2:33][C:34]([N:36]3[CH2:40][CH2:39][CH2:38][C@H:37]3[C:41](=[O:47])[NH:42][CH:43]3[CH2:46][CH2:45][CH2:44]3)=[O:35])[C:29]3[C:24](=[CH:25][C:26]([CH3:48])=[CH:27][CH:28]=3)[N:23]=2)=[O:21])[CH2:14][CH2:15][C:16]([NH:73][NH2:74])=[O:17])[CH2:8][CH2:7]1)=[O:3])[CH3:56]

Participants

6

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68602655HCID 68602655, compound

Product 1

HCID 68600217HCID 68600217, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 100 mg of 4-[(S)-4-Carboxy-2-({4-[2-((S)-2-cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-7-methyl-quinoline-2-carbonyl}-amino)-butyryl]-piperazine-1-carboxylic acid ethyl ester, 48 mg of TOTU and 67 mg of NEM in 2 ml of DCM, 10 mg of hydrazine hydrate was added and the reaction mixture was stirred for 16 h at RT. Then, the reaction mixture was diluted with water and extracted with DCM. The combined organic phases were dried over MgSO4 and the solvents were removed under reduced pressure. The crude product was used for the next reaction step. Yield: 101 mg.

Workup

  1. extractionextracted with DCM
  2. dry with materialThe combined organic phases were dried over MgSO4
  3. customthe solvents were removed under reduced pressure
  4. customThe crude product was used for the next reaction step

Sources & evidence

ORD record
ord-2a05e67a4dfd4827ad8f76d156e1c562
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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