1-Hydroxybenzotriazole → HCID 59381886, compound

HRID 2355091Notes

Reaction equation

HRID 2355091 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[NH:12][C:13]([C:15]1[CH:16]=[CH:17][C:18]([CH3:24])=[C:19]([CH:23]=1)[C:20](O)=[O:21])=[O:14].C(N(C(C)C)CC)(C)C.ON1C2C=CC=CC=2N=N1.CCN=C=NCCCN(C)C.Cl.[CH3:56][N:57]1[CH2:62][CH2:61][N:60]([C:63]2[CH:68]=[CH:67][C:66]([NH:69][C:70]3[N:75]=[CH:74][C:73]([NH2:76])=[CH:72][N:71]=3)=[CH:65][CH:64]=2)[CH2:59][CH2:58]1>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:9])[F:10])=[CH:4][C:3]=1[NH:12][C:13](=[O:14])[C:15]1[CH:16]=[CH:17][C:18]([CH3:24])=[C:19]([C:20]([NH:76][C:73]2[CH:74]=[N:75][C:70]([NH:69][C:66]3[CH:65]=[CH:64][C:63]([N:60]4[CH2:59][CH2:58][N:57]([CH3:56])[CH2:62][CH2:61]4)=[CH:68][CH:67]=3)=[N:71][CH:72]=2)=[O:21])[CH:23]=1

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 24823422HCID 24823422, compoundHCID 59381875HCID 59381875, compound

Product 1

HCID 59381886HCID 59381886, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 16×100 mm vial was charged with 5-((2-fluoro-5-(trifluoromethyl)phenyl)carbamoyl)-2-methylbenzoic acid 36 (0.100 g, 0.293 mmol), dichloromethane (3 mL), diisopropylethylamine (0.200 ml, 1.15 mmol), 1-hydroxybenzotriazole (0.0396 g, 0.293 mmol), EDC.HCl (0.0562 g, 0.293 mmol), and N2-(4-(4-methylpiperazin-1-yl)phenyl)pyrimidine-2,5-diamine (0.0875 g, 0.308 mmol), and the mixture stirred at room temperature for 24 hours. The reaction mixture was purified via column chromatography on silica gel (gradient elution with 0 to 20% methanol in dichloromethane) to afford N1-(2-fluoro-5-(trifluoromethyl)phenyl)-4-methyl-N3-(2-(4-(4-methylpiperazin-1-yl)phenylamino)pyrimidin-5-yl)isophthalamide 37 as a light yellow solid. MS m/z found 608 [MH+]; calc. for C31H29F4N7O2=607.60.

Workup

  1. customThe reaction mixture was purified via column chromatography on silica gel (gradient elution with 0 to 20% methanol in dichloromethane)

Sources & evidence

ORD record
ord-ded293c391a840d396b8d0fd1686cd83
Source dataset
uspto-grants-2010_07
Patent number
US07754717B2

Reaction notes

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