4-Methylmorpholine → HCID 67075245, compound

HRID 718937Notes

Reaction equation

HRID 718937 reaction equation
[CH2:1]([NH:8][C:9]([NH:11][N:12]([CH2:14][C:15]([OH:17])=O)[CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN1CCOCC1.OC1C2N=NNC=2C=CC=1.Cl.CN(C)CCCN=C=NCC.[NH2:47][C@@H:48]([CH3:68])[C:49]([N:51]([CH2:61][C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1)[C@@H:52]([CH3:60])[CH:53]([O:57][CH2:58][CH3:59])[O:54][CH2:55][CH3:56])=[O:50]>CN(C=O)C.C(Cl)Cl.CN(C1C=CN=CC=1)C.CC(=O)OCC>[CH2:1]([NH:8][C:9](=[O:10])[NH:11][N:12]([CH2:14][C:15]([NH:47][C@@H:48]([CH3:68])[C:49]([N:51]([CH2:61][C:62]1[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=1)[C@@H:52]([CH3:60])[CH:53]([O:57][CH2:58][CH3:59])[O:54][CH2:55][CH3:56])=[O:50])=[O:17])[CH3:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

10

Reactant 5

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 533974892-(2-(Benzylcarbamoyl)-1-methylhydrazinyl)acetic acidHCID 67075209HCID 67075209, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 67075245HCID 67075245, compound

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(2-(benzylcarbamoyl)-1-methylhydrazinyl)acetic acid (Compound VI-3) 115 mg (0.49 mmol) and NMM (N-methylmorpholine) 0.33 ml were added in DMF 1.5 ml. Then, HOBt (hydroxybenzotriazole) 88 mg (0.65 mmol) and EDCI (N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride) 125 mg (0.65 mmol) were added and stirred at room temperature for 10 min. Compound (S)-2-amino-N-benzyl-N—((S)-1,1-diethoxypropan-2-yl)propanamide (IV-10) 100 mg (0.32 mmol) in DCM 1.5 ml and DMAP 4.1 mg (0.03 mmol) were added. The mixture was stirred overnight at room temperature. The mixture was diluted with EA 30 ml and washed with 10% citric acid 15 ml, sat. NaHCO3 15 ml and brine 15 ml. The solvent was removed in vacuum to give crude product, which was used directly in the next step.

Workup

  1. stirringThe mixture was stirred overnight at room temperature
  2. washwashed with 10% citric acid 15 ml, sat. NaHCO3 15 ml and brine 15 ml
  3. customThe solvent was removed in vacuum
  4. customto give crude product, which

Sources & evidence

ORD record
ord-091fb18c13384536911b66b7044b3f91
Source dataset
uspto-grants-2015_11
Patent number
US09193734B2

Reaction notes

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