Methylamine → HCID 86732459, compound

HRID 1776433Notes

Reaction equation

HRID 1776433 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH2:11][N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([C:21]2[N:26]=[C:25]([NH:27][C:28]3[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=3)[C:24]([O:34][CH3:35])=[CH:23][N:22]=2)=[N:13]1)[C:5]([OH:7])=[O:6].CN.O1CCCC1.F[P-](F)(F)(F)(F)F.[CH3:50][N:51](C(ON1C2=NC=CC=C2N=N1)=[N+](C)C)C.C(N(C(C)C)C(C)C)C>CS(C)=O>[CH:5]([OH:7])=[O:6].[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH2:11][N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([C:21]2[N:26]=[C:25]([NH:27][C:28]3[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=3)[C:24]([O:34][CH3:35])=[CH:23][N:22]=2)=[N:13]1)[C:5]([NH:51][CH3:50])=[O:7]

Participants

7

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 86732458HCID 86732458, compound

Product 1

HCID 86732459HCID 86732459, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

130.9 mg of 3-chloro-4-({3-[5-methoxy-4-(pyridin-4-ylamino)pyrimidin-2-yl]-1H-indazol-1-yl}methyl)benzoic acid (28-1, 0.269 mmol, 1. eq.), 1.1 ml of dimethylsulfoxide, 269 μl of 2 M methanamine in tetrahydrofuran (0.538 mmol, 2 eq.), 225 mg of N-[(dimethylamino)(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yloxy)methylidene]-N-methylmethanaminium hexafluorophosphate (HATU; 0.591 mmol, 2.2 eq.) and 140 μl of N-ethyl-N-(propan-2-yl)propan-2-amine (0.806 mmol, 3 eq.) were stirred at 50° C. bath temperature for 5 hours. The reaction mixture was filtered off and purified by preparative HPLC to yield 91 mg (0.17 mmol, 62%) of the analytically pure target compound.

Workup

  1. filtrationThe reaction mixture was filtered off
  2. custompurified by preparative HPLC
  3. customto yield 91 mg (0.17 mmol, 62%) of the analytically pure target compound

Sources & evidence

ORD record
ord-25afcaf88eb84d37bc74385234ac13c7
Source dataset
uspto-grants-2016_02
Patent number
US09265763B2

Reaction notes

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