Diisopropylethylamine → 5-Chloro-2-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)-amino]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl}-benzonitrile

HRID 657801Notes

Reaction equation

HRID 657801 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH2:20][CH2:19][C:13]3[N:14]=[CH:15][N:16]=[C:17](Cl)[C:12]=3[CH2:11]2)=[C:6]([CH:9]=1)[C:7]#[N:8].[N:21]1[CH:22]=[CH:23][N:24]2[CH:29]=[CH:28][C:27]([CH2:30][NH2:31])=[CH:26][C:25]=12.C(N(CC)C(C)C)(C)C>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH2:20][CH2:19][C:13]3[N:14]=[CH:15][N:16]=[C:17]([NH:31][CH2:30][C:27]4[CH:28]=[CH:29][N:24]5[CH:23]=[CH:22][N:21]=[C:25]5[CH:26]=4)[C:12]=3[CH2:11]2)=[C:6]([CH:9]=1)[C:7]#[N:8]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 55289825Imidazo(1,2-a)pyridin-7-ylmethanamineHCID 598406875-Chloro-2-(4-chloro-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)benzonitrile

Product 1

HCID 250595425-Chloro-2-{4-[(imidazo[1,2-a]pyridin-7-ylmethyl)-amino]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl}-benzonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A reaction mixture of 5-chloro-2-(4-chloro-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)benzonitrile (250 mg, 0.82 mmol) and imidazo[1,2-a]pyridin-7-ylmethanamine (270 mg, 1.83 mmol) in acetonitrile (10 mL) and N,N-diisopropylethylamine (1.0 mL, 5.7 mmol) was subjected to microwave irradiation at 185° C. for 4 h. The reaction mixture was concentrated and purified by semi-preparative HPLC (100×20.2 mm, C18 column; 40-60% CH3CN-water [10 mM Et2NH]) to yield a light yellow solid.

Workup

  1. customirradiation at 185° C. for 4 h
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by semi-preparative HPLC (100×20.2 mm, C18 column; 40-60% CH3CN-water [10 mM Et2NH])
  4. customto yield a light yellow solid

Sources & evidence

ORD record
ord-df4cf00ccf694b16ae5aed8df9df4d89
Source dataset
uspto-grants-2011_12
Patent number
US08076345B2

Reaction notes

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