Methylamine → HCID 24877276, compound

HRID 333405Notes

Reaction equation

HRID 333405 reaction equation
[CH3:1][C:2]1([CH3:33])[O:6]/[C:5](=[C:7]2/[C:8](=[O:26])[NH:9][C:10]3[C:15]/2=[CH:14][CH:13]=[C:12]([S:16][C:17]2[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=2[C:19](O)=[O:20])[CH:11]=3)/[CH:4]=[C:3]1[N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.CN.C1COCC1.[CH3:41][N:42](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[CH3:33][C:2]1([CH3:1])[O:6]/[C:5](=[C:7]2/[C:8](=[O:26])[NH:9][C:10]3[C:15]/2=[CH:14][CH:13]=[C:12]([S:16][C:17]2[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=2[C:19]([NH:42][CH3:41])=[O:20])[CH:11]=3)/[CH:4]=[C:3]1[N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1

Participants

8

Reactant 5

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 24877383HCID 24877383, compound

Product 1

HCID 24877276HCID 24877276, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-{[(3E)-3-(5,5-dimethyl-4-morpholin-4-ylfuran-2(5H)-ylidene)-2-oxo-2,3-dihydro-1H-indol-6-yl]thio}benzoic acid in 5 mL of anhydrous DMF, were added 2M methylamine in THF solution (0.066 mL, 0.13 mmol), HBTU (49 mg, 0.13 mmol) and DIPEA (31 mg, 0.24 mmol). The reaction mixture was stirred at room temperature for 15 minutes and poured into 100 mL of water. The precipitates were filtered, washed with water and dried to give the crude product as a brown solid. Purification of the crude product by silica gel chromatography eluted with a gradient of 5-15% MeOH in CHCl3 afforded 2-{[(3E)-3-(5,5-dimethyl-4-morpholin-4-ylfuran-2(5H)-ylidene)-2-oxo-2,3-dihydro-1H-indol-6-yl]thio}-N-methylbenzamide as brown solid. Yield: 6 mg, 12%.

Workup

  1. filtrationThe precipitates were filtered
  2. washwashed with water
  3. customdried
  4. customto give the crude product as a brown solid
  5. customPurification of the crude product by silica gel chromatography
  6. washeluted with a gradient of 5-15% MeOH in CHCl3

Sources & evidence

ORD record
ord-7aa921dba9154a1dbafff52f32900b96
Source dataset
uspto-grants-2014_11
Patent number
US08877923B2

Reaction notes

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