Methylamine → HCID 68627578, compound

HRID 572616Notes

Reaction equation

HRID 572616 reaction equation
[C:1]([C:3]1[C:4]([I:17])=[C:5]([C:14]([OH:16])=O)[S:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)#[N:2].[CH3:18][N:19](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.CN.C1COCC1>CN(C=O)C.O>[C:1]([C:3]1[C:4]([I:17])=[C:5]([C:14]([NH:19][CH3:18])=[O:16])[S:6][C:7]=1[N:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1)#[N:2]

Participants

8

Reactant 5

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 42609111HCID 42609111, compound

Product 1

HCID 68627578HCID 68627578, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-cyano-3-iodo-5-morpholin-4-ylthiophene-2-carboxylic acid (7.1 g, 19.4 mmol) in DMF (195 mL) were added HATU (8.9 g, 23.4 mmol) and DIPEA (4.1 mL, 23.3 mmol). The reaction mixture was allowed to stir at rt for 1 h and a 2.0 M solution of methylamine in THF (19.4 mL, 38.8 mmol) was added. The reaction mixture was allowed to stir at rt for 30 min and water was added. A precipitate formed and was filtered and dried to give 4-cyano-3-iodo-N-methyl-5-morpholin-4-ylthiophene-2-carboxamide (6.4 g, 87%). LCMS: (FA) ES+ 378.0, ES− 376.1. 1H NMR (400 MHz, d6-DMSO) δ: 7.92 (m, 1H), 3.72-3.76 (m, 4H), 3.47-3.51 (m, 4H) and 2.73 (d, 3H).

Workup

  1. stirringto stir at rt for 30 min
  2. customA precipitate formed
  3. filtrationwas filtered
  4. customdried

Sources & evidence

ORD record
ord-373992951c7d40fdaa13f83627f2ddf5
Source dataset
uspto-grants-2015_05
Patent number
US09029411B2

Reaction notes

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