Methanol → Amuvatinib

HRID 2052830Notes

Reaction equation

HRID 2052830 reaction equation
[N:1]1([C:7]2[C:8]3[O:15][C:14]4[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=4[C:9]=3[N:10]=[CH:11][N:12]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.N1C=CC=CC=1.[Cl-].[O:27]1[C:31]2[CH:32]=[CH:33][C:34]([CH2:36][NH:37][CH:38]=[S:39])=[CH:35][C:30]=2[O:29][CH2:28]1.CO>ClCCl>[O:27]1[C:31]2[CH:32]=[CH:33][C:34]([CH2:36][NH:37][C:38]([N:4]3[CH2:5][CH2:6][N:1]([C:7]4[C:8]5[O:15][C:14]6[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=6[C:9]=5[N:10]=[CH:11][N:12]=4)[CH2:2][CH2:3]3)=[S:39])=[CH:35][C:30]=2[O:29][CH2:28]1

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 23685424-(Piperazin-1-yl)benzofuro[3,2-d]pyrimidineHCID 86601006N-Benzo[1,3]dioxol-5-ylmethyl-thioformamide chloride

Product 1

HCID 11282283Amuvatinib

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-piperazinobenzofurano[3,2-d]pyrimidine (200 mg, 0.79 mmol) and pyridine (0.5 mL, 7.9 mmol) in dichloromethane (20 mL) was added a solution of product 1c in dichloromethane (20 mL) and this was stirred overnight. Methanol was added to quench excess thiophosgene, and the residue after removal of solvent was purified by silica gel column chromatography eluting with 5% methanol/dichloromethane and further recrystallized from dichloromethane/hexane to give 150 mg (37%).

Workup

  1. customto quench excess thiophosgene
  2. customthe residue after removal of solvent
  3. customwas purified by silica gel column chromatography
  4. washeluting with 5% methanol/dichloromethane
  5. customfurther recrystallized from dichloromethane/hexane
  6. customto give 150 mg (37%)

Sources & evidence

ORD record
ord-e59f47fd250841f8a2044ebc8a023d61
Source dataset
uspto-grants-2008_02
Patent number
US07326712B2

Reaction notes

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