Isopropylamine → HCID 68715475, compound

HRID 2101205Notes

Reaction equation

HRID 2101205 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].Br[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([B:13]2[O:17][C:16]([CH3:19])([CH3:18])[C:15]([CH3:21])([CH3:20])[O:14]2)=[CH:9][CH:8]=1>COCOC>[CH3:18][C:16]1([CH3:19])[C:15]([CH3:20])([CH3:21])[O:14][B:13]([C:10]2[CH:9]=[CH:8][C:7]([CH2:6][NH:4][CH:1]([CH3:3])[CH3:2])=[CH:12][CH:11]=2)[O:17]1

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 37345062-(4-(Bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 68715475HCID 68715475, compound

Reagents, catalysts & solvents 1

HCID 8020DimethoxymethaneSolvent

Procedure

Isopropylamine (0.5 ml) was added dropwise to a solution of 2-[4-(bromomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.5 g) in dimethoxymethane (10 ml) and the resulting solution was stirred at room temperature for 18 h. The reaction mixture was evaporated under reduced pressure and used immediately. b) 2-[(Aminocarbonyl)amino]-5-{4-[(isopropylamino)methyl]phenyl}thiophene-3-carboxamide A solution of N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]propan-2-amine (0.46 g), 2-[(aminocarbonyl)amino]-5-bromothiophene-3-carboxamide (0.2 g) and sodium carbonate (0.32 g) in a DME (15 ml)/water (1.5 ml) mixture was heated to 80° C. under an argon stream. Tetrakis-(triphenylphosphine)palladium(0) (5.1 g) was then added and the reaction was stirred at 90° C. for 4 h, cooled and evaporated under reduced pressure. The residue was partitioned between DCM and saturated sodium carbonate and the solid interlayer was filtered and washed with water. The pure product was obtained by cation exchange chromatography eluting with ammonia/methanol mixtures (0.06 g). MS (ES) 333 (M+H)+. 1H NMR (DMSO-D6) 1.0 (d, 6H), 2.7 (m, 1H), 3.7 (s, 2H), 6.9 (br, 2H), 7.3 (br, 1H), 7.4 (d, 2H), 7.5 (d, 2H), 7.7 (br, 1H), 7.75 (s, 1H), 11.0 (s, 1H).

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. temperatureb) 2-[(Aminocarbonyl)amino]-5-{4-[(isopropylamino)methyl]phenyl}thiophene-3-carboxamide A solution of N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]propan-2-amine (0.46 g), 2-[(aminocarbonyl)amino]-5-bromothiophene-3-carboxamide (0.2 g) and sodium carbonate (0.32 g) in a DME (15 ml)/water (1.5 ml) mixture was heated to 80° C. under an argon stream
  3. additionTetrakis-(triphenylphosphine)palladium(0) (5.1 g) was then added
  4. stirringthe reaction was stirred at 90° C. for 4 h
  5. temperaturecooled
  6. customevaporated under reduced pressure
  7. customThe residue was partitioned between DCM and saturated sodium carbonate
  8. filtrationthe solid interlayer was filtered
  9. washwashed with water
  10. customThe pure product was obtained by cation exchange chromatography
  11. washeluting with ammonia/methanol mixtures (0.06 g)

Sources & evidence

ORD record
ord-5754d52bfc3b45f0bdda81a1b1e1494e
Source dataset
uspto-grants-2009_08
Patent number
US07572826B2

Reaction notes

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