Methoxyacetic Acid → HCID 22479002, compound

HRID 2090243Notes

Reaction equation

HRID 2090243 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][CH2:8][CH2:9][CH2:10][NH:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=[CH:14][C:13]=1[NH2:22])([CH3:4])([CH3:3])[CH3:2].CCN=C=NC[CH2:30][CH2:31]N(C)C.C1C=CC2N(O)N=NC=2C=1.C[O:46][CH2:47][C:48](O)=O>CN1C(=O)CCC1.C(OCC)C.CCN(CC)CC>[C:1]([O:5][C:6](=[O:23])[NH:7][CH2:8][CH2:9][CH2:10][N:11]1[C:12]2[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:15]=[CH:14][C:13]=2[N:22]=[C:48]1[CH2:47][O:46][CH2:30][CH3:31])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 12251Methoxyacetic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 66958404HCID 66958404, compound

Product 1

HCID 22479002HCID 22479002, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8471TriethylamineSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
40 °C

Procedure

The product from example 1 step (iii) (790 mg) was dissolved in NMP (5 mL), then EDCI (1.44 g), HOBt (1 g), methoxyacetic acid (0.71 mL) and Et3N (1 mL) were added. The mixture was stirred at 40° C. for 15 h then heated at 60° C. for 5 h. After cooling to rt, the crude mixture was dissolved in diethyl ether, washed with brine, dried and evaporated under reduced pressure, which afforded 600 mg of the subtitle product.

Workup

  1. temperaturethen heated at 60° C. for 5 h
  2. temperatureAfter cooling to rt
  3. washwashed with brine
  4. customdried
  5. customevaporated under reduced pressure, which

Sources & evidence

ORD record
ord-e1577b1ade724ea18ba1e7ebdf63d5df
Source dataset
uspto-grants-2013_05
Patent number
US08436178B2

Reaction notes

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