N,N-Dimethyl-1,3-propanediamine → HCID 22021869, compound

HRID 1793409Notes

Reaction equation

HRID 1793409 reaction equation
[F:1][C:2]1[C:7]2[S:8][CH:9]=[C:10]3[C:14](=[O:15])[N:13]([C:16]4[CH:24]=[CH:23][C:19]([C:20]([OH:22])=O)=[CH:18][CH:17]=4)[N:12]=[C:11]3[C:6]=2[CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(=[N+](C)C)N(C)C)C2C=CC=CC=2N=N1.[CH3:58][N:59]([CH3:64])[CH2:60][CH2:61][CH2:62][NH2:63]>CC(N(C)C)=O>[CH3:58][N:59]([CH3:64])[CH2:60][CH2:61][CH2:62][NH:63][C:20](=[O:22])[C:19]1[CH:23]=[CH:24][C:16]([N:13]2[C:14](=[O:15])[C:10]3=[CH:9][S:8][C:7]4[C:2]([F:1])=[CH:3][CH:4]=[CH:5][C:6]=4[C:11]3=[N:12]2)=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22021863HCID 22021863, compound

Product 1

HCID 22021869HCID 22021869, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

4-(6-Fluoro-3-oxothiochromeno[4,3-c]pyrazol-2(3H)-yl)benzoic acid (41 mg, 0.12 mmol) was dissolved in anhydrous dimethyl-acetamide(1 ml). Diisopropyl-ethyl amine (46 mg, 0.36 mmol, 62 μl) was added followed by [(benzotriazol-1-yloxy)-dimethylamino-methylene]-dimethyl-ammonium hexafluoro phosphate (65 mg, 0.17 mmol) and 3-dimethylaminopropylamine (12 mg, 0.12 mmol). The mixture was stirred at room temperature overnight and purified by preparative HPLC. The title compound was isolated as a brown solid. LCMS: m/z 425 [M+H]+.

Workup

  1. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-7211bc94ac1349c49ceee66c042b8421
Source dataset
uspto-grants-2006_07
Patent number
US07081456B2

Reaction notes

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