Methylamine → HCID 71554580, compound

HRID 1776423Notes

Reaction equation

HRID 1776423 reaction equation
[Cl:1][C:2]1[C:10]([CH2:11][N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([C:21]3[N:26]=[C:25]([NH:27][C:28]4[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=4)[C:24]([O:34][CH3:35])=[CH:23][N:22]=3)=[N:13]2)=[C:9]([Cl:36])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.F[P-](F)(F)(F)(F)F.[CH3:44][N:45](C(ON1C2=NC=CC=C2N=N1)=[N+](C)C)C.C(N(C(C)C)C(C)C)C.CN>CS(C)=O.O1CCCC1>[Cl:1][C:2]1[C:10]([CH2:11][N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([C:21]3[N:26]=[C:25]([NH:27][C:28]4[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=4)[C:24]([O:34][CH3:35])=[CH:23][N:22]=3)=[N:13]2)=[C:9]([Cl:36])[CH:8]=[CH:7][C:3]=1[C:4]([NH:45][CH3:44])=[O:6]

Participants

7

Reactant 4

HCID 6329Methylamine2×HCID 81531Diisopropylethylamine2×HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2×HCID 71554489HCID 71554489, compound

Product 1

HCID 71554580HCID 71554580, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

100 mg of 2,4-dichloro-3-({3-[5-methoxy-4-(pyridin-4-ylamino)pyrimidin-2-yl]-1H-indazol-1-yl}methyl)benzoic acid (19-1, 0.192 mmol, 1. eq.) were dissolved in 0.953 ml of dry dimethyl sulfoxide. 80.2 mg of N-[(dimethylamino)(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yloxy)methylidene]-N-methylmethanaminium hexafluorophosphate (0.211 mmol, 1.1 eq.), 67 μl of N-ethyl-N-(propan-2-yl)propan-2-amine (0.384 mmol, 2 eq.) and 96 μl of 2 N methyl amine in tetrahydrofuran were added in this sequence. The reaction mixture was stirred at room temperature for 18 hours. 80.2 mg of N-[(dimethylamino)(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yloxy)-methylidene]-N-methylmethanaminium hexafluorophosphate (0.211 mmol, 1.1 eq.), 67 μl of N-ethyl-N-(propan-2-yl)propan-2-amine (0.384 mmol, 2 eq.) and 96 μl of 2 N methyl amine in tetrahydrofuran were added in this sequence again twice and stirred each time at room temperature for 24 hours. The reaction mixture was stirred at 50° C. bath temperature for further 2 hours. Then the mixture was filtered off purified by preparative HPLC to yield 15 mg (0.03 mmol, 14.3%) of the analytically pure target compound.

Workup

  1. stirringstirred each time at room temperature for 24 hours
  2. stirringThe reaction mixture was stirred at 50° C. bath temperature for further 2 hours
  3. filtrationThen the mixture was filtered off
  4. custompurified by preparative HPLC
  5. customto yield 15 mg (0.03 mmol, 14.3%) of the analytically pure target compound

Sources & evidence

ORD record
ord-98a098b5eb7c43a2a40ec05f015ad2a6
Source dataset
uspto-grants-2016_02
Patent number
US09265763B2

Reaction notes

Loading…