Ammonia → (S)-2-(1-((5-(1-(2-Hydroxybenzyl)-1H-pyrazol-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

HRID 1052792Notes

Reaction equation

HRID 1052792 reaction equation
C[O:2][C:3]1[CH:51]=[CH:50][CH:49]=[CH:48][C:4]=1[CH2:5][N:6]1[CH:10]=[CH:9][C:8]([C:11]2[C:19]3[C:18]([NH:20][C@H:21]([C:23]4[N:28]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)[C:27](=[O:35])[C:26]5=[C:36]([CH3:39])[CH:37]=[CH:38][N:25]5[N:24]=4)[CH3:22])=[N:17][CH:16]=[N:15][C:14]=3[N:13](COCC[Si](C)(C)C)[CH:12]=2)=[N:7]1.B(Br)(Br)Br.N>ClCCl>[OH:2][C:3]1[CH:51]=[CH:50][CH:49]=[CH:48][C:4]=1[CH2:5][N:6]1[CH:10]=[CH:9][C:8]([C:11]2[C:19]3[C:18]([NH:20][C@H:21]([C:23]4[N:28]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)[C:27](=[O:35])[C:26]5=[C:36]([CH3:39])[CH:37]=[CH:38][N:25]5[N:24]=4)[CH3:22])=[N:17][CH:16]=[N:15][C:14]=3[NH:13][CH:12]=2)=[N:7]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 25134Boron tribromideHCID 131736239(S)-2-(1-((5-(1-(2-Methoxybenzyl)-1H-pyrazol-3-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

Product 1

HCID 136929380(S)-2-(1-((5-(1-(2-Hydroxybenzyl)-1H-pyrazol-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-oneYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-2-(1-((5-(1-(2-Methoxybenzyl)-1H-pyrazol-3-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (53 mg, 0.08 mmol) was treated with boron tribromide (1M in dichloromethane, 750 μL, 0.75 mmol) in dichloromethane (1.0 mL) and then with a solution of ammonia (7N in methanol, 750 μl, 5.25 mmol) according to the method described in Example 41. The residue was purified using SP1® Purification System (reverse phase, 0% to 100% water-methanol/acetonitrile 1:1) to obtain 20 mg (48% yield) of the title compound.

Workup

  1. customThe residue was purified
  2. customSP1® Purification System (reverse phase, 0% to 100% water-methanol/acetonitrile 1:1)

Sources & evidence

ORD record
ord-5b20919ddada45fb950bd5ffbbe8c1b5
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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