Triethylamine → HCID 44540254, compound

HRID 1926192Notes

Reaction equation

HRID 1926192 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.[F:55][C:56]1[CH:61]=[CH:60][C:59]([NH2:62])=[C:58]([NH2:63])[CH:57]=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:62][C:59]3[CH:60]=[CH:61][C:56]([F:55])=[CH:57][C:58]=3[NH2:63])=[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 1645844-Fluorobenzene-1,2-diamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 574954166-(2-(9H-fluoren-9-ylidene)acetamido)hexanoic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 44540254HCID 44540254, compoundYield 79%

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-fluoro-o-phenylenediamine (151 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 (350 mg, 79% yield) as a brown solid. 1H NMR (DMSO-d6) δ1.39 (m, 2H, CH2), 1.57 (m, 2H, CH2), 1.63 (m, 2H, CH2), 2.31 (t, J=8.0 Hz, 2H, CH2CO), 3.26 (m, 2H, NCH2), 5.13 (s, 2H, benzene-NH2), 6.26 (t, J=8.0 Hz, 1H, Ar—H), 6.46 (d, J=8.0 Hz, 1H, Ar—H), 7.08 (s, 1H, ═CH—CO and Ar—H), 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), 8.53 (t, J=4.0 Hz, 1H, CONH), 8.69 (d, J=8.0 Hz, 1H, Ar—H), 9.03 (s, 1H, benzene-NH). LC-MS (m/z) 444 (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-765c9d7f4c1d4928b933bf62d7fb73a1
Source dataset
uspto-grants-2012_05
Patent number
US08178577B2

Reaction notes

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