Diisopropylethylamine → HCID 67516261, compound

HRID 919597Notes

Reaction equation

HRID 919597 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][CH2:10][C:11]([N:13]2[CH2:18][CH2:17][CH2:16][C@H:15]([NH:19][CH3:20])[CH2:14]2)=[O:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl[C:22]1[CH:27]=[CH:26][N:25]=[C:24]([NH2:28])[N:23]=1.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[NH2:28][C:24]1[N:23]=[C:22]([N:19]([CH3:20])[C@H:15]2[CH2:16][CH2:17][CH2:18][N:13]([C:11](=[O:12])[CH2:10][NH:9][C:4]3[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=3)[CH2:14]2)[CH:27]=[CH:26][N:25]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2233322-Amino-4-chloropyrimidineHCID 69676444HCID 69676444, compound

Product 1

HCID 67516261HCID 67516261, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of 2-(3,5-dichlorophenylamino)-1-((S)-3-(methylamino)piperidin-1-yl)ethanone (0.3 mg, 1.0 mmol), 4-chloropyrimidin-2-amine (60 mg, 0.5 mmol), DIEA (0.17 mL, 1.9 mmol) in DMF (2 mL) was heated to 100° C. for 2 days. The reaction mixture was diluted with EtOAc and washed with water. The organic layer was dried over Na2SO4 and evaporated in vacuo to give the crude compound which was purified (silica gel, gradient MeOH in CH2Cl2) to give the (20 mg, 5.2%). 1H NMR (400 MHz, CD3OD): δ 7.77-7.73 (m, 1H), 6.64-6.56 (m, 3H), 6.10-6.00 (m, 1H), 4.58-4.45 (m, 2H), 4.10-3.84 (m, 3H), 2.96 (s, 3H), 2.58-2.81 (m, 1H), 2.03-1.90 (m, 4H), 1.60-1.48 (m, 1H). LC-MS: m/z [M+1]=409 & [M+23]=431.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-78a1098529674ec5bc7f6f420519377e
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

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