Ammonia → HCID 90102599, compound

HRID 1052810Notes

Reaction equation

HRID 1052810 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([S:46]([NH:49][CH3:50])(=[O:48])=[O:47])[CH:6]=[CH:7][C:8]=1[C:9]1[C:17]2[C:16]([NH:18][C@H:19]([C:21]3[N:26]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:25](=[O:33])[C:24]4=[C:34]([CH3:37])[CH:35]=[CH:36][N:23]4[N:22]=3)[CH3:20])=[N:15][CH:14]=[N:13][C:12]=2[N:11](COCC[Si](C)(C)C)[CH:10]=1.B(Br)(Br)Br.N>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]([S:46]([NH:49][CH3:50])(=[O:48])=[O:47])[CH:6]=[CH:7][C:8]=1[C:9]1[C:17]2[C:16]([NH:18][C@H:19]([C:21]3[N:26]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[C:25](=[O:33])[C:24]4=[C:34]([CH3:37])[CH:35]=[CH:36][N:23]4[N:22]=3)[CH3:20])=[N:15][CH:14]=[N:13][C:12]=2[NH:11][CH:10]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 25134Boron tribromideHCID 90102906HCID 90102906, compound

Product 1

HCID 90102599HCID 90102599, compoundYield 23.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-3-Methoxy-N-methyl-4-(4-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)benzenesulfonamide (45 mg, 0.06 mmol) was treated with boron tribromide (1M in dichloromethane, 2.0 mL, 2.00 mmol) in dichloromethane (1 mL) and then with a solution of ammonia (7N in methanol, 5.0 mL, 35.0 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 8 mg (22% 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-a20914b080d44eab8cc8c86983178856
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

Loading…