Triethylamine → 6-(3-((5-fluoro-2-oxoindolin-3-ylidene)methyl)benzamido)-N-(2-amino-4-fluorophenyl)hexanamide

HRID 251699Notes

Reaction equation

HRID 251699 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[CH:12][C:13]1[CH:14]=[C:15]([CH:27]=[CH:28][CH:29]=1)[C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24](O)=[O:25])=[O:17].Cl.C(N=C=NCCCN(C)C)C.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C.[F:59][C:60]1[CH:65]=[CH:64][C:63]([NH2:66])=[C:62]([NH2:67])[CH:61]=1>[Cl-].[Na+].O.CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[CH:12][C:13]1[CH:14]=[C:15]([CH:27]=[CH:28][CH:29]=1)[C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([NH:66][C:63]1[CH:64]=[CH:65][C:60]([F:59])=[CH:61][C:62]=1[NH2:67])=[O:25])=[O:17]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 1645844-Fluorobenzene-1,2-diamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 690325116-(3-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)benzamido)hexanoic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 690327076-(3-((5-fluoro-2-oxoindolin-3-ylidene)methyl)benzamido)-N-(2-amino-4-fluorophenyl)hexanamideYield 74%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

6-(3-((5-fluoro-2-oxoindolin-3-ylidene)methyl)benzamido)hexanoic acid (396 mg, 1 mmol), and 8 ml of DMF were stirred at room temperature while 1-Ethyl-3-(3-dimethylamino-propyl)carbodiimide hydrochloride (394 mg, 2 mmol), hydroxybenzotriazole (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 (373 mg, 74% yield) as a brown solid. 1H NMR (DMSO-d6)δ1.36 (m, 2H, CH2), 1.59 (m, 4H, CH2), 2.30 (t, J=8.0 Hz, 2H, CH2CO), 3.28 (t, J=8.0 Hz, 2H, NCH2), 5.12 (s, 2H, benzene-NH2), 6.26 (t, J=8.0 Hz, 1H, Ar—H), 6.46 (d, J=8.0 Hz, 1H, Ar—H), 6.87 (m, 1H, Ar—H), 7.12 (m, 3H, Ar—H), 7.64 (m, 1H, Ar—H), 7.73 (s, 0.6×1H, vinyl-H), 7.83 (m, 1H, Ar—H), 7.94 (m, 1H, Ar—H), 8.16 (s, 0.4×1H, vinyl-H), 8.57 (m, 1H, Ar—H), 9.02 (s, 1H, benzene-NH), 10.68 (s, 1H, CONH). LC-MS (m/z) 505 (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-bad9dc1eeed240a0a3baf15269a666f7
Source dataset
uspto-grants-2011_01
Patent number
US07863315B2

Reaction notes

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