Dimethylformamide → HCID 9889287, compound

HRID 991425Notes

Reaction equation

HRID 991425 reaction equation
Cl.CN(C)CCCN=C=NCC.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][C:23]=1[O:24][CH3:25])[C:18]([OH:20])=O.[NH2:26][C:27]1[CH:28]=[C:29]([NH:34][C:35](=[O:45])[C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([N:42]([CH3:44])[CH3:43])[CH:37]=2)[CH:30]=[CH:31][C:32]=1[F:33].CN(C=O)C>C(Cl)Cl.CN(C)C1C=CN=CC=1.O>[CH3:43][N:42]([CH3:44])[C:38]1[CH:37]=[C:36]([CH:41]=[CH:40][CH:39]=1)[C:35]([NH:34][C:29]1[CH:30]=[CH:31][C:32]([F:33])=[C:27]([NH:26][C:18](=[O:20])[C:17]2[CH:21]=[CH:22][C:23]([O:24][CH3:25])=[C:15]([O:14][CH3:13])[CH:16]=2)[CH:28]=1)=[O:45]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 7121Veratric AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18413852HCID 18413852, compound

Product 1

HCID 9889287HCID 9889287, compoundYield 37.5%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.12 g) in methylene chloride (5 ml) was added to a stirred mixture of 3,4-dimethoxybenzoic acid (0.91 g), N-(3-amino-4-fluorophenyl)-3-dimethylaminobenzamide (0.14 g), DMF (2 ml) and 4-dimethylaminopyridine (0.004 g). The reaction mixture was stirred at ambient temperature for 18 hours. Water (20 ml) and methylene chloride (10 ml) were added. The organic phase was washed with a saturated aqueous sodium bicarbonate solution, dried (MgSO4) and evaporated. The residual oil was purified by column chromatography on silica gel using a 49:1 mixture of methylene chloride and methanol as eluent. The material so obtained was triturated under diethyl ether. There was thus obtained the title compound (0.084 g) as a colourles solid, m.p. 187-188° C.; NMR Spectrum: (CDCl3) 3.02 (s, 6H), 3.97 (s, 6H), 6.86 (m, 1H), 6.93 (d, 1H), 7.09 (d, 1H), 7.16 (t, 1H), 7.25 (m, 1H), 7.32 (t, 1H), 7.41 (m, 1 H), 7.5 (d, 1H), 7.88 (m, 1H), 7.97 (s, 1H), 8.04 (s, 1H), 8.42 (m, 1H);

Workup

  1. washThe organic phase was washed with a saturated aqueous sodium bicarbonate solution
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe residual oil was purified by column chromatography on silica gel using
  5. additiona 49:1 mixture of methylene chloride and methanol as eluent
  6. customThe material so obtained
  7. customwas triturated under diethyl ether

Sources & evidence

ORD record
ord-5e95ab4fa0004e22a9d2b14cf5ef64c8
Source dataset
uspto-grants-2002_10
Patent number
US06465455B1

Reaction notes

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