2,3-Dihydro-1,4-benzodioxin-6-carbaldehyde → HCID 21104578, compound

HRID 1354225Notes

Reaction equation

HRID 1354225 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH:11]=O)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:27][O:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[N:35]=[CH:34][N:33]=[C:32]2[O:39][CH2:40][CH:41]1[CH2:46][CH2:45][CH:44]([NH2:47])[CH2:43][CH2:42]1>ClC(Cl)C>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][NH:47][CH:44]3[CH2:45][CH2:46][CH:41]([CH2:40][O:39][C:32]4[C:31]5[C:36](=[CH:37][CH:38]=[C:29]([O:28][CH3:27])[CH:30]=5)[N:35]=[CH:34][N:33]=4)[CH2:42][CH2:43]3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 2481272,3-Dihydro-1,4-benzodioxin-6-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 21104633HCID 21104633, compound

Product 1

HCID 21104578HCID 21104578, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

2,3-Dihydro-benzo[1,4]dioxin-6-carbaldehyde (0.045 g, 0.27 mmol) and then sodium triacetoxyborohydride (0.08 g, 0.377 mmol) were added to a solution of 4-(6-methoxyquinazolin-4-yloxymethyl)-cyclohexylamine (0.07 g, 0.25 mmol) in dichloroethane (1 ml). The reaction mixture was stirred for 2 hours and then filtered over Hydromatrix (wetted with NaHCO3 solution, 2 ml) and subsequently washed with dichloromethane. The filtrate was concentrated to dryness by rotary evaporation. The residue was purified by column chromatography on silica gel (dichloromethane/MeOH 9/1 and then dichloromethane/MeOH 6/1).

Workup

  1. filtrationfiltered over Hydromatrix (wetted with NaHCO3 solution, 2 ml)
  2. washsubsequently washed with dichloromethane
  3. concentrationThe filtrate was concentrated to dryness by rotary evaporation
  4. customThe residue was purified by column chromatography on silica gel (dichloromethane/MeOH 9/1

Sources & evidence

ORD record
ord-6232b1f8b99b429080bd3aec2d8ce79c
Source dataset
uspto-grants-2007_05
Patent number
US07223776B2

Reaction notes

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