1423057-50-4 → HCID 178420284, compound

HRID 1506173Notes

Reaction equation

HRID 1506173 reaction equation
[CH2:1]([NH:9][CH:10]1[CH2:15][CH2:14][CH:13]([C:16]2[N:17]=[N:18][N:19]3[C:24]=2[C:23]2[CH:25]=[CH:26][NH:27][C:22]=2[N:21]=[CH:20]3)[CH2:12][CH2:11]1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1(C2CCC(NC3C=CC(C#N)=CC=3)CC2)N=NN2C=1C1C=CNC=1N=C2>>[CH2:1]([NH:9][C@H:10]1[CH2:15][CH2:14][C@@H:13]([C:16]2[N:17]=[N:18][N:19]3[C:24]=2[C:23]2[CH:25]=[CH:26][NH:27][C:22]=2[N:21]=[CH:20]3)[CH2:12][CH2:11]1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:1]([NH:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([C:16]2[N:17]=[N:18][N:19]3[C:24]=2[C:23]2[CH:25]=[CH:26][NH:27][C:22]=2[N:21]=[CH:20]3)[CH2:12][CH2:11]1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 1362273441423057-50-4HCID 136341309HCID 136341309, compound

Product 2

HCID 178420284HCID 178420284, compoundYield 16%HCID 178420285HCID 178420285, compoundYield 11%

Procedure

The reactions in Synthetic Examplea 134 were carried out in substantially the same manners except that N-phenethyl-4-(7H-pyrrolo[3,2-e][1,2,3]triazolo[1,5-c]pyrimidin-1-yl)cyclohexanamine obtained in Synthetic Examplea 123 was used instead of 4-{[4-(7H-pyrrolo[3,2-e][1,2,3]triazolo[1,5-c]pyrimidin-1-yl)cyclohexyl]amino}benzonitrile to give cis-N-phenethyl-4-(7H-pyrrolo[3,2-e][1,2,3]triazolo[1,5-c]pyrimidin-1-yl)cyclohexanamine (Synthetic Examplea 135a; colorless solid, 3.22 mg, yield 16%) in a less polar fraction and trans-N-phenethyl-4-(7H-pyrrolo[3,2-e][1,2,3]triazolo[1,5-c]pyrimidin-1-yl)cyclohexanamine (Synthetic Examplea 135b; colorless solid, 2.52 mg, yield 11%) in a more polar fraction.

Workup

  1. customobtained in Synthetic Examplea 123

Sources & evidence

ORD record
ord-b18467f4753248dc893193108487156e
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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