Methanol → HCID 59682922, compound

HRID 1668693Notes

Reaction equation

HRID 1668693 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[O:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)[N:14]=[CH:13][N:12]=[C:11]2[O:27][C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[NH:33][C:32]([CH3:37])=[CH:31]2.CCN(C(C)C)C(C)C.CO>ClCCl>[Cl:1][CH2:2][C:3]([N:24]1[CH2:23][CH2:22][N:21]([CH2:20][CH2:19][O:18][C:17]2[CH:16]=[C:15]3[C:10]([C:11]([O:27][C:28]4[CH:29]=[C:30]5[C:34](=[CH:35][CH:36]=4)[NH:33][C:32]([CH3:37])=[CH:31]5)=[N:12][CH:13]=[N:14]3)=[CH:9][C:8]=2[O:7][CH3:6])[CH2:26][CH2:25]1)=[O:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 6577Chloroacetyl chlorideHCID 81531DiisopropylethylamineHCID 59682923HCID 59682923, compound

Product 1

HCID 59682922HCID 59682922, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Chloroacetyl chloride (0.09 ml) was added dropwise to a solution of 6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]-7-[2-(piperazin-1-yl)ethoxy]quinazoline (0.45 g), prepared as described in Example 13, and PS-DIEA resin (0.66 g) in dichloromethane (15 ml). After 1 hour at ambient temperature, methanol was added and the reaction mixture was filtered. Solvents were removed by evaporation in vacuum and the residue was triturated under diethyl ether, filtrated and dried to give 7-{2-[4-(chloroacetyl)piperazin-1-yl]ethoxy}-6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]quinazoline (0.36 g) as a solid.

Workup

  1. customprepared
  2. filtrationthe reaction mixture was filtered
  3. customSolvents were removed by evaporation in vacuum
  4. customthe residue was triturated under diethyl ether
  5. filtrationfiltrated
  6. customdried

Sources & evidence

ORD record
ord-e2ec950677f743adbe0b3b3c147262e0
Source dataset
uspto-grants-2011_08
Patent number
US07989460B2

Reaction notes

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