Ammonia → HCID 90102672, compound

HRID 1052735Notes

Reaction equation

HRID 1052735 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][C:10]2[C:18]3[C:17]([NH:19][C@H:20]([C:22]4[N:27]([C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)[C:26](=[O:34])[C:25]5=[C:35]([CH3:38])[CH:36]=[CH:37][N:24]5[N:23]=4)[CH3:21])=[N:16][CH:15]=[N:14][C:13]=3[N:12](COCC[Si](C)(C)C)[CH:11]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br.N>ClCCl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([S:9][C:10]2[C:18]3[C:17]([NH:19][C@H:20]([C:22]4[N:27]([C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)[C:26](=[O:34])[C:25]5=[C:35]([CH3:38])[CH:36]=[CH:37][N:24]5[N:23]=4)[CH3:21])=[N:16][CH:15]=[N:14][C:13]=3[NH:12][CH:11]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 25134Boron tribromideHCID 131736253HCID 131736253, compound

Product 1

HCID 90102672HCID 90102672, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-2-(1-((5-((4-Methoxyphenyl)thio)-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 (65 mg, 0.10 mmol) was treated with boron tribromide (1M in dichloromethane, 894 μL, 0.99 mmol) in dichloromethane (1.3 mL) and then with a solution of ammonia (7N in methanol, 1.3 ml, 9.10 mmol) according to the method described in Example 41. The residue was purified using SP1® Purification System (0% to 100% dichloromethane ethyl acetate) to obtain 24 mg (48% yield) of the title compound.

Workup

  1. customThe residue was purified
  2. customSP1® Purification System (0% to 100% dichloromethane ethyl acetate)

Sources & evidence

ORD record
ord-2068e8db488e4cfe8d4468eeb7ec2f52
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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