Diisopropylethylamine → HCID 25059288, compound

HRID 657799Notes

Reaction equation

HRID 657799 reaction equation
Cl[C:2]1[C:3]2[CH2:11][N:10]([C:12]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:13]=3[C:14]#[N:15])[CH2:9][CH2:8][C:4]=2[N:5]=[CH:6][N:7]=1.[O:21]1[C:25]2[CH:26]=[CH:27][C:28]([CH2:30][NH2:31])=[CH:29][C:24]=2[N:23]=[CH:22]1.C(N(CC)C(C)C)(C)C>C(#N)C>[O:21]1[C:25]2[CH:26]=[CH:27][C:28]([CH2:30][NH:31][C:2]3[C:3]4[CH2:11][N:10]([C:12]5[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:13]=5[C:14]#[N:15])[CH2:9][CH2:8][C:4]=4[N:5]=[CH:6][N:7]=3)=[CH:29][C:24]=2[N:23]=[CH:22]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 50989749HCID 50989749, compoundHCID 598406882-(4-Chloro-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-5-methylbenzonitrile

Product 1

HCID 25059288HCID 25059288, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A reaction mixture of 2-(4-chloro-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-5-methylbenzonitrile (100 mg, 0.35 mmol) and benzo[d]oxazol-5-ylmethanamine (150 mg, 0.41 mmol) in acetonitrile (3 mL) and N,N-diisopropylethylamine (0.37 mL, 2.1 mmol) was subjected to microwave irradiation at 185° C. for 2.5 h. The reaction mixture was concentrated and purified by preparative HPLC (100×20.2 mm, C18 column; 30-60% CH3CN-water [10 mM Et2NH]) to yield a light yellow solid.

Workup

  1. customirradiation at 185° C. for 2.5 h
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by preparative HPLC (100×20.2 mm, C18 column; 30-60% CH3CN-water [10 mM Et2NH])
  4. customto yield a light yellow solid

Sources & evidence

ORD record
ord-893d9c8a7607425697c0ecc8cacc4c1c
Source dataset
uspto-grants-2011_12
Patent number
US08076345B2

Reaction notes

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