Dimethylformamide → HCID 14372553, compound

HRID 620254Notes

Reaction equation

HRID 620254 reaction equation
[H-].[Na+].[NH2:3][C:4]1[C:19]([Cl:20])=[CH:18][C:7]([C:8]([NH:10][CH2:11][CH2:12][N:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[O:9])=[C:6]([O:21][CH:22]([CH3:26])[C:23](=[O:25])[CH3:24])[CH:5]=1.[H][H].[CH2:29](Br)[CH:30]=C.[CH3:33]N(C=O)C>>[NH2:3][C:4]1[C:19]([Cl:20])=[CH:18][C:7]([C:8]([NH:10][CH2:11][CH2:12][N:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[O:9])=[C:6]([O:21][C:22]([CH3:33])([CH2:26][CH:29]=[CH2:30])[C:23](=[O:25])[CH3:24])[CH:5]=1

Participants

6

Reactant 5

HCID 6228Dimethylformamide2×HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 59692BatanoprideHCID 178418361HCID 178418361, compound

Product 1

HCID 14372553HCID 14372553, compound

Procedure

To a stirred suspension of sodium hydride (0.2 g of 60%, 5 mmoles, washed with n-pentane) in DMF (10 ml) was added dropwise a solution of 4-amino-2-(butan-2-on-3-yl)oxy-5-chloro-N-[2-(diethylamino)ethyl]benzamide (1.78 g, 5 mmoles) in DMF (10 ml). After hydrogen evolution subsided, allyl bromide (690 mg, 5.7 mmoles) was added and the mixture stirred for 72 hours, followed by partition between water and methylene chloride. The organic phase was washed with water, dried and concentrated. The residue was chromatographed on deactivated silica, using methylene chloride (100), methanol (4), ammonia (0.5). The appropriate fractions were combined to give 0.58 g of crude product as a heavy oil. This was crystallized from ether to give the title compound as a white solid, mp 138°-140°. The NMR spectrum (90 MHz) in CDCl3 gave the following resonances: δ 8.24 (s, 1H); 8.0 (bs, 1H); 5.92 (s, 1H); 5.9-5.0 (m, 4H); 4.38 (bs, 2H); 3.58 (m, 2H); 3.0-2.3 (m, 8H); 2.28 (s, 3H); 1.62 (s, 3H); 1.04 (t, 6H).

Workup

  1. customby partition between water and methylene chloride
  2. washThe organic phase was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was chromatographed on deactivated silica
  6. customto give 0.58 g of crude product as a heavy oil
  7. customThis was crystallized from ether

Sources & evidence

ORD record
ord-380f26c652d04cc795fc0e18f67b56ab
Source dataset
uspto-grants-1989_04
Patent number
US04820715

Reaction notes

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