Triethylamine → HCID 57972061, compound

HRID 1926214Notes

Reaction equation

HRID 1926214 reaction equation
[CH:1]1[C:14]2[C:13](=[CH:15][C:16](O)=[O:17])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl.C(N=C=NCCCN(C)C)C.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C.Cl.[CH3:49][O:50][C:51](=[O:58])[CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][NH2:57]>[Cl-].[Na+].O.CN(C=O)C>[CH3:49][O:50][C:51](=[O:58])[CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][NH:57][C:16](=[O:17])[CH:15]=[C:13]1[C:14]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[O:6][C:7]2[C:12]1=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11499324Methyl 6-aminohexanoate hydrochlorideHCID 67520945HCID 67520945, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 57972061HCID 57972061, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

2-(9H-xanthen-9-ylidene)acetic acid (238 mg, 1 mmol) and 8 ml of DMF were stirred at room temperature while 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (394 mg, 2 mmol), hydroxybenzo-triazole (162 mg, 1.2 mmol), triethylamine (404 mg, 4 mmol) and 6-aminocaproic acid methyl ester hydrochloride (219 mg, 1.2 mmol) were added. The mixture was stirred for 24 hours at room temperature. The mixture was diluted with 400 mL of brine. The solids were collected by vacuum filtration, washed with water and dried under vacuum to give the title compound (321 mg, 88% yield) as a white solid. LC-MS (m/z) 366 (M+1).

Workup

  1. additionwere added
  2. filtrationThe solids were collected by vacuum filtration
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-4a477fdedd084afcbde612bc153746b1
Source dataset
uspto-grants-2012_05
Patent number
US08178577B2

Reaction notes

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