Pyridine → HCID 131736227, compound

HRID 1052608Notes

Reaction equation

HRID 1052608 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[C:4]([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]([CH2:40][O:41][CH2:42][CH2:43][Si:44]([CH3:47])([CH3:46])[CH3:45])[CH:12]=2)[CH:3]=1.N1C=CC=CC=1.[S:54](Cl)(=[O:57])(=[O:56])[NH2:55]>O1CCCC1>[CH3:39][C:36]1[CH:37]=[CH:38][N:25]2[C:26]=1[C:27](=[O:35])[N:28]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]([C@@H:21]([NH:20][C:18]1[C:19]3[C:11]([C:4]4[CH:3]=[C:2]([NH:1][S:54]([NH2:55])(=[O:57])=[O:56])[CH:10]=[C:9]5[C:5]=4[CH:6]=[CH:7][NH:8]5)=[CH:12][N:13]([CH2:40][O:41][CH2:42][CH2:43][Si:44]([CH3:45])([CH3:47])[CH3:46])[C:14]=3[N:15]=[CH:16][N:17]=1)[CH3:22])=[N:24]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 24499Chlorosulfamic acidHCID 131736205HCID 131736205, compound

Product 1

HCID 131736227HCID 131736227, compoundYield 49.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)-2-(1-((5-(6-Amino-1H-indol-4-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 (84 mg, 0.13 mmol) was treated with pyridine (15 μL, 0.18 mmol) and sulfamoyl chloride (18 mg, 0.16 mmol) in tetrahydrofuran (1.0 ml) according to the method described in Preparation 175 but stirring at room temperature during 48 h. The residue was purified using SP1® Purification System (0% to 50% hexane-ethyl acetate) to obtain 47 mg (49% yield) of the title compound.

Workup

  1. customdescribed in Preparation 175
  2. customThe residue was purified
  3. customSP1® Purification System (0% to 50% hexane-ethyl acetate)

Sources & evidence

ORD record
ord-19d5be5c710346b6917d4b61cd506cc2
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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