Hydrochloric Acid → HCID 90370342, compound

HRID 2176006Notes

Reaction equation

HRID 2176006 reaction equation
[CH:1]1([N:4]([CH2:9][C:10]2[CH:11]=[C:12]([CH:46]=[CH:47][CH:48]=2)[C:13]([NH:15][C:16]2[S:17][C:18]3[CH2:45][CH2:44][CH2:43][CH2:42][C:19]=3[C:20]=2[C:21]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][C:32]3[CH:41]=[CH:40][C:35]([C:36]([O:38][CH3:39])=[O:37])=[CH:34][CH:33]=3)=[CH:26][CH:25]=2)=[O:22])=[O:14])[CH2:5][CH2:6][NH:7][CH3:8])[CH2:3][CH2:2]1.[CH3:49][O:50][CH2:51][CH2:52][O:53][CH2:54][C:55]([OH:57])=O.CCN=C=NCCCN(C)C.Cl>O.CN(C=O)C>[CH:1]1([N:4]([CH2:9][C:10]2[CH:11]=[C:12]([CH:46]=[CH:47][CH:48]=2)[C:13]([NH:15][C:16]2[S:17][C:18]3[CH2:45][CH2:44][CH2:43][CH2:42][C:19]=3[C:20]=2[C:21]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][C:32]3[CH:41]=[CH:40][C:35]([C:36]([O:38][CH3:39])=[O:37])=[CH:34][CH:33]=3)=[CH:26][CH:25]=2)=[O:22])=[O:14])[CH2:5][CH2:6][N:7]([CH3:8])[C:55](=[O:57])[CH2:54][O:53][CH2:52][CH2:51][O:50][CH3:49])[CH2:2][CH2:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27642(2-Methoxyethoxy)acetic acidHCID 90370187HCID 90370187, compound

Product 1

HCID 90370342HCID 90370342, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 194 mg of methyl 4-[2-(4-{[(2-{[3-({cyclopropyl[2-(methylamino)ethyl]amino}methyl)benzoyl]amino}-4,5,6,7-tetrahydro-1-benzothiophen-3-yl)carbonyl]amino}phenyl)ethyl]benzoate, 0.050 mL of (2-methoxyethoxy)acetic acid, 84 mg of WSC.hydrochloride, and 5.0 mL of DMF was stirred for 15 hours at room temperature. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (5% methanol/chloroform), thereby obtaining 200 mg of methyl 4-[2-(4-{[(2-{[3-(11-cyclopropyl-8-methyl-7-oxo-2,5-dioxa-8,11-diazadodecan-12-yl)benzoyl]amino}-4,5,6,7-tetrahydro-1-benzothiophen-3-yl)carbonyl]amino}phenyl)ethyl]benzoate.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (5% methanol/chloroform)

Sources & evidence

ORD record
ord-429afc8f18ea42c38700d2dcf517577a
Source dataset
uspto-grants-2015_06
Patent number
US09062032B2

Reaction notes

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