Ammonium Chloride → (5)-4-(3-(3-Cyclopropyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin-8-yl)-8-((2,4-dimethoxybenzyl)amino)imidazo[1,5-a]pyrazin-1-yl)benzamide

HRID 62470Notes

Reaction equation

HRID 62470 reaction equation
[CH:1]1([C:4]2[N:8]3[CH2:9][CH2:10][CH2:11][C@@H:12]([C:13]4[N:17]5[CH:18]=[CH:19][N:20]=[C:21]([NH:22][CH2:23][C:24]6[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:25]=6[O:32][CH3:33])[C:16]5=[C:15]([C:34]5[CH:42]=[CH:41][C:37]([C:38](O)=[O:39])=[CH:36][CH:35]=5)[N:14]=4)[C:7]3=[N:6][N:5]=2)[CH2:3][CH2:2]1.[NH4+].[Cl-].C[N:46](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH:1]1([C:4]2[N:8]3[CH2:9][CH2:10][CH2:11][C@@H:12]([C:13]4[N:17]5[CH:18]=[CH:19][N:20]=[C:21]([NH:22][CH2:23][C:24]6[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:25]=6[O:32][CH3:33])[C:16]5=[C:15]([C:34]5[CH:42]=[CH:41][C:37]([C:38]([NH2:46])=[O:39])=[CH:36][CH:35]=5)[N:14]=4)[C:7]3=[N:6][N:5]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 90303981(5)-4-(3-(3-Cyclopropyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin-8-yl)-8-((2,4-dimethoxybenzyl)amino)imidazo[1,5-a]pyrazin-1-yl)benzoic acid

Product 1

HCID 90304213(5)-4-(3-(3-Cyclopropyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin-8-yl)-8-((2,4-dimethoxybenzyl)amino)imidazo[1,5-a]pyrazin-1-yl)benzamideYield 46.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (S)-4-(3-(3-cyclopropyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin-8-yl)-8-((2,4-dimethoxybenzyl)amino)imidazo[1,5-a]pyrazin-1-yl)benzoic acid (130 mg, 0.23 mmol) in DMF (2 mL) was added NH4Cl (37 mg, 0.69 mmol), TEA (93 mg, 0.92 mmol) and HATU (175 mg, 0.46 mmol). The mixture was stirred at RT overnight. After the reaction was completed, the solvent was evaporated and the residue was purified by Pre-TLC to give (S)-4-(3-(3-cyclopropyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin-8-yl)-8-((2,4-dimethoxybenzyl)amino)imidazo[1,5-a]pyrazin-1-yl)benzamide (60 mg, yield 46%).

Workup

  1. customthe solvent was evaporated
  2. customthe residue was purified by Pre-TLC

Sources & evidence

ORD record
ord-f938d3d6039346d2a668c4e697224bb7
Source dataset
uspto-grants-2016_09
Patent number
US09446130B2

Reaction notes

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