Potassio isocyanate → HCID 131736228, compound

HRID 1052610Notes

Reaction equation

HRID 1052610 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([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]([CH2:39][O:40][CH2:41][CH2:42][Si:43]([CH3:46])([CH3:45])[CH3:44])[CH:11]=2)[CH:5]=[N:6][C:7]=1[O:8][CH3:9].[N-:47]=[C:48]=[O:49].[K+]>O.C(O)(=O)C>[CH3:9][O:8][C:7]1[C:2]([NH:1][C:48]([NH2:47])=[O:49])=[CH:3][C:4]([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]([CH2:39][O:40][CH2:41][CH2:42][Si:43]([CH3:46])([CH3:45])[CH3:44])[CH:11]=2)=[CH:5][N:6]=1

Participants

5

Reactant 2

HCID 11051572Potassio isocyanateHCID 131736141HCID 131736141, compound

Product 1

HCID 131736228HCID 131736228, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a suspension of (S)-2-(1-((5-(5-amino-6-methoxypyridin-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 (92 mg, 0.14 mmol) in water (0.75 mL) and acetic acid (1.2 mL) was added potassium isocyanate (20 mg, 0.25 mmol) according to the method described in Preparation 181. The residue was purified using SP1® Purification System (0% to 5% dichloromethane methanol) to obtain 61 mg (53% yield, 86% purity) of the title compound.

Workup

  1. customdescribed in Preparation 181
  2. customThe residue was purified
  3. customSP1® Purification System (0% to 5% dichloromethane methanol)

Sources & evidence

ORD record
ord-42bb5d0376bf4508896a583822a3347e
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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