Triethylamine → 6-(2-(9H-fluoren-9-ylidene)acetamido)-N-(2-amino-4-methoxyphenyl)hexanamide

HRID 1926196Notes

Reaction equation

HRID 1926196 reaction equation
[CH:1]1[C:13]2[C:12](=[CH:14][C:15]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23](O)=[O:24])=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[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.[CH3:55][O:56][C:57]1[CH:62]=[CH:61][C:60]([NH2:63])=[C:59]([NH2:64])[CH:58]=1>[Cl-].[Na+].O.CN(C=O)C>[CH:10]1[C:11]2[C:12](=[CH:14][C:15]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([NH:63][C:60]3[CH:61]=[CH:62][C:57]([O:56][CH3:55])=[CH:58][C:59]=3[NH2:64])=[O:24])=[O:16])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 1534044-Methoxy-o-phenylenediamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 574954166-(2-(9H-fluoren-9-ylidene)acetamido)hexanoic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 445403426-(2-(9H-fluoren-9-ylidene)acetamido)-N-(2-amino-4-methoxyphenyl)hexanamideYield 73%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

6-(2-(9H-fluoren-9-ylidene)acetamido)hexanoic acid (335 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), hydroxy-benzotriazole (162 mg, 1.2 mmol), triethylamine (404 mg, 4 mmol) and 4-methoxy-o-phenylenediamine (166 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 (332 mg, 73% yield) as a brown solid. 1H NMR (DMSO-d6) δ1.39 (m, 2H, CH2), 1.55 (m, 2H, CH2), 1.62 (m, 2H, CH2), 2.29 (t, J=8.0 Hz, 2H, CH2CO), 3.27 (m, 2H, NCH2), 3.62 (s, 3H, OCH3), 4.84 (s, 2H, benzene-NH2), 6.08 (d, J=8.0 Hz, 1H, Ar—H), 6.28 (s, 1H, Ar—H), 6.95 (d, J=8.0 Hz, 1H, Ar—H), 7.10 (s, 1H, ═CH—CO), 7.33 (m, 2H, Ar—H), 7.40 (m, 2H, Ar—H), 7.76 (d, J=8.0 Hz, 1H, Ar—H), 7.82 (m, 2H, Ar—H), 8.58 (t, J=4.0 Hz, 1H, CONH), 8.72 (d, J=8.0 Hz, 1H, Ar—H), 9.02 (s, 1H, benzene-NH). LC-MS (m/z) 456 (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-ae10b5630b1843199174499c272c7255
Source dataset
uspto-grants-2012_05
Patent number
US08178577B2

Reaction notes

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