1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 73041735, compound

HRID 402923Notes

Reaction equation

HRID 402923 reaction equation
[NH2:1][C@@H:2]1[C:13]2[C:7](=[CH:8][CH:9]=[C:10]([S:15][CH3:16])[C:11](=[O:14])[CH:12]=2)[C:6]2[C:17]([O:26][CH3:27])=[C:18]([O:24][CH3:25])[C:19]([O:21][CH2:22][CH3:23])=[CH:20][C:5]=2[CH2:4][CH2:3]1.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[F:50][C:51]1[C:59]([CH2:60][OH:61])=[CH:58][CH:57]=[CH:56][C:52]=1[C:53](O)=[O:54]>ClCCl.C(OCC)(=O)C.C(#N)C>[CH2:22]([O:21][C:19]1[C:18]([O:24][CH3:25])=[C:17]([O:26][CH3:27])[C:6]2[C:7]3[C:13]([CH:2]([NH:1][C:53](=[O:54])[C:52]4[CH:56]=[CH:57][CH:58]=[C:59]([CH2:60][OH:61])[C:51]=4[F:50])[CH2:3][CH2:4][C:5]=2[CH:20]=1)=[CH:12][C:11](=[O:14])[C:10]([S:15][CH3:16])=[CH:9][CH:8]=3)[CH3:23]

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27744892-fluoro-3-(hydroxymethyl)benzoic AcidHCID 27960291-Hydroxybenzotriazole hydrateHCID 11545531HCID 11545531, compound

Product 1

HCID 73041735HCID 73041735, compoundYield 5,586%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

163 g (421 mmol, 1.0 eq) of (7S)-7-amino-3-ethoxy-1,2,-dimethoxy-10-methylsulfanyl-6,7-dihydro-5H-benzo[a]heptalene-9-one was dissolved in 1.4 l of dichloromethane, and then 105 g (547 mmol, 1.3 eq) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide and 5.7 g (42.1 mmol, 0.1 eq) of 1-hydroxybenzotriazol hydrate were added. 93.6 g (54 7 mmol, 1.3 eq) of 2-fluoro-3-(hydroxymethyl)benzoic acid was added and then stirred for 2 hours at a room temperature. After completing the reaction, the reaction mixture was washed with purified water; dehydrated with magnesium sulfate anhydrous; and then concentrated under reduced pressure to obtain a product in a yellow solid phase. The mixed solution of 300 ml of acetonitrile and 250 ml of ethyl acetate was added to the obtained product, and then stirred for 30 minutes at a room temperature and for 2 hours at 0° C. The resulting solid was filtered, washed with ethyl acetate, and then dried to obtain 211 g of N-(3-ethoxy-1,2-dimethoxy-10-methylsulfanyl-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptalene-7-yl)-2-fluoro-3-hydroxymethylbenzamide in a yellow solid phase.

Workup

  1. customthe reaction
  2. washthe reaction mixture was washed with purified water
  3. concentrationand then concentrated under reduced pressure
  4. customto obtain a product in a yellow solid phase
  5. stirringstirred for 30 minutes at a room temperature and for 2 hours at 0° C
  6. filtrationThe resulting solid was filtered
  7. washwashed with ethyl acetate
  8. customdried

Sources & evidence

ORD record
ord-983a2128005748c3878c24340e0c6e2b
Source dataset
uspto-grants-2014_06
Patent number
US08742160B2

Reaction notes

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