Methylamine → HCID 118060573, compound

HRID 2274815Notes

Reaction equation

HRID 2274815 reaction equation
N1C[CH:3]([CH2:5][N:6]2[CH:10]=[C:9]([C:11]3[C:19]4[C:14](=[CH:15][C:16]([F:20])=[CH:17][CH:18]=4)[NH:13][CH:12]=3)[CH:8]=[N:7]2)C1.CN(C([O:28]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CC[N:47]([CH2:50]C)CC.CN>C1COCC1.O>[F:20][C:16]1[CH:15]=[C:14]2[C:19]([C:11]([C:9]3[CH:8]=[N:7][N:6]([CH2:5][C:3]([NH:47][CH3:50])=[O:28])[CH:10]=3)=[CH:12][NH:13]2)=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 6329MethylamineHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 118059901HCID 118059901, compound

Product 1

HCID 118060573HCID 118060573, compoundYield 26.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-(6-fluoro-1H-indol-3-yl)-1H-pyrazol-1-yl)acetic acid (Example 6; 120 mg; 0.46 mmol) in THF (25 mL) was added HATU (350 mg; 0.92 mmol) and Et3N (279 mg; 2.76 mmol) under nitrogen. The reaction mixture was stirred for 10 minutes before methylamine (0.5 mL; 1.0 mmol; 2 M in THF) was added dropwise. The reaction mixture was stirred at r.t. overnight, diluted with water (20 mL) and extracted with EtOAc (20 mL×3). The combined organic layers were concentrated, and purified by preparative TLC (EtOAc) to afford 33 mg (26%) of the title product as a white solid.

Workup

  1. additionwas added dropwise
  2. extractionextracted with EtOAc (20 mL×3)
  3. concentrationThe combined organic layers were concentrated
  4. custompurified by preparative TLC (EtOAc)

Sources & evidence

ORD record
ord-ce936de90b044dda884158cb42742dbc
Source dataset
uspto-grants-2015_09
Patent number
US09126984B2

Reaction notes

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