Methylamine → HCID 11281862, compound

HRID 2076236Notes

Reaction equation

HRID 2076236 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([O:15][C:16]3[CH:31]=[CH:30][C:19]4[C:20]([C:24]([NH:26][CH:27]5[CH2:29][CH2:28]5)=[O:25])=[C:21]([CH3:23])[O:22][C:18]=4[CH:17]=3)=[CH:10][CH:11]=[N:12]2)=[CH:7][CH:6]=1.[CH3:32][NH2:33]>C1COCC1.CS(C)=O>[CH:27]1([NH:26][C:24]([C:20]2[C:19]3[CH:30]=[CH:31][C:16]([O:15][C:9]4[C:8]5[C:13](=[CH:14][C:5]([O:4][CH2:3][CH2:2][NH:33][CH3:32])=[CH:6][CH:7]=5)[N:12]=[CH:11][CH:10]=4)=[CH:17][C:18]=3[O:22][C:21]=2[CH3:23])=[O:25])[CH2:29][CH2:28]1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 11477177HCID 11477177, compound

Product 1

HCID 11281862HCID 11281862, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of compound 90-1 (100 mg, 0.21 mmol) and 0.3 ml of methylamine 90-J (R′═CH3, R′═H) in THF (2N) in DMSO (2 ml) was heated to 60° C. for 1 hour. The reaction mixture was purified by HPLC (Dionex System) using 10-50% CH3CN/H2O+0.1% AcOH over 30 minutes to give N-cyclopropyl-2-methyl-6-({7-[2-(methylamino)ethoxy]quinolin-4-yl}oxy)-1-benzofuran-3-carboxamide 90 (42 mg).

Workup

  1. customThe reaction mixture was purified by HPLC (Dionex System)
  2. customover 30 minutes

Sources & evidence

ORD record
ord-388ed3033ccc416c9e2a9517687d9207
Source dataset
uspto-grants-2011_04
Patent number
US07923457B2

Reaction notes

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