Acetaldehyde ammonia → 6-[(2-{[7-(2,4-Dichlorophenyl)imidazo[1,2-c]pyrimidin-5-yl]oxy}ethyl)amino]pyridine-3-carbonitrile

HRID 2171580Notes

Reaction equation

HRID 2171580 reaction equation
Cl[C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[CH:5]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])[N:3]=1.[OH:19][CH2:20][CH2:21][NH:22][C:23]1[N:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=1.ClC1N=CC(C#N)=CC=1.NC(O)C>>[Cl:18][C:12]1[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:11]=1[C:4]1[N:3]=[C:2]([O:19][CH2:20][CH2:21][NH:22][C:23]2[N:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=2)[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[CH:5]=1

Participants

5

Reactant 4

HCID 522583Acetaldehyde ammoniaHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 221428216-(2-Hydroxyethylamino)nicotinonitrileHCID 59312932HCID 59312932, compound

Product 1

HCID 593130506-[(2-{[7-(2,4-Dichlorophenyl)imidazo[1,2-c]pyrimidin-5-yl]oxy}ethyl)amino]pyridine-3-carbonitrile

Procedure

In analogy to the procedure described for Example 90, 35 mg (48% of theory) of the product are obtained starting from 50 mg (0.17 mmol) of 5-chloro-7-(2,4-dichlorophenyl)imidazo-[1,2-c]pyrimidine (Example 6A) by reaction with 38 mg (0.23 mmol) of 6-[(2-hydroxyethyl)amino]pyridine-3-carbonitrile, which can be prepared in analogy to the synthesis of Example 48A from 6-chloropyridine-3-carbonitrile and aminoethanol, after subsequent purification by preparative HPLC.

Workup

  1. customare obtained
  2. customafter subsequent purification by preparative HPLC

Sources & evidence

ORD record
ord-2563b03e4f924751bc13b306993d8c47
Source dataset
uspto-grants-2015_06
Patent number
US09051323B2

Reaction notes

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