1,2-Dichloroethane → HCID 118093098, compound

HRID 2207360Notes

Reaction equation

HRID 2207360 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:19]2[CH:20]=[CH:21][C:22]([CH2:25][C:26]([OH:28])=O)=[N:23][CH:24]=2)[CH:5]=[C:6]([NH:8][C:9]2[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][N:10]=2)[CH:7]=1.[CH3:29][NH:30][CH3:31].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>O1CCOCC1>[CH3:29][N:30]([CH3:31])[C:26](=[O:28])[CH2:25][C:22]1[CH:21]=[CH:20][C:19]([C:4]2[CH:5]=[C:6]([NH:8][C:9]3[N:14]=[C:13]([C:15]([F:17])([F:16])[F:18])[CH:12]=[CH:11][N:10]=3)[CH:7]=[C:2]([CH3:1])[CH:3]=2)=[CH:24][N:23]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 674DimethylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 118092787HCID 118092787, compound

Product 1

HCID 118093098HCID 118093098, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-(5-(3-methyl-5-((4-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)pyridin-2-yl)acetic acid (8.4 mg, 0.020 mmol), dimethylamine (0.05 ml, 0.100 mmol, 2M), EDC (8.6 mg, 0.045 mmol), HOBT (7.8 mg, 0.051 mmol), DIEA (10 μl, 0.057 mmol) in 1,4-dioxane (0.8 ml) was stirred at room temperature for 16 hours. The mixture was purified by reversed phase HPLC to afford N,N-dimethyl-2-(5-(3-methyl-5-((4-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)pyridin-2-yl)acetamide (8.4 mg, 0.016 mmol). MS ESI calc'd. for C21H21F3N5O [M+H]+ 416. found 416. 1H NMR (600 MHz, CD3OD): δ 8.97 (s, 1H), 8.71 (d, J=4.8 Hz, 1H), 8.62 (d, J=6.0 Hz, 1H), 8.09 (s, 1H), 7.89 (d, J=6.0 Hz, 1H), 7.60 (s, 1H), 7.26 (s, 1H), 7.13 (d, J=4.8 Hz, 1H), 4.25 (s, 2H), 3.18 (s, 3H), 3.00 (s, 3H), 2.43 (s, 3H).

Workup

  1. customThe mixture was purified by reversed phase HPLC

Sources & evidence

ORD record
ord-20eb1a2e13b24b118d071f3269ca3603
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

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