2-(Trifluoromethyl)aniline → HCID 10161019, compound

HRID 1064569Notes

Reaction equation

[F:1][C:2]([F:11])([F:10])[C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5].C(N(CC)C(C)C)(C)C.[CH3:21][C@H:22]1[N:27]([C:28]2[C:29]3[CH:36]=[CH:35][S:34][C:30]=3[N:31]=[CH:32][N:33]=2)[C@@H:26]([CH3:37])[CH2:25][N:24]([CH2:38][C:39](O)=[O:40])[CH2:23]1.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>O1CCOCC1.CN(C)C1C=CN=CC=1>[CH3:21][C@H:22]1[N:27]([C:28]2[C:29]3[CH:36]=[CH:35][S:34][C:30]=3[N:31]=[CH:32][N:33]=2)[C@@H:26]([CH3:37])[CH2:25][N:24]([CH2:38][C:39]([NH:5][C:4]2[CH:6]=[CH:7][CH:8]=[CH:9][C:3]=2[C:2]([F:10])([F:11])[F:1])=[O:40])[CH2:23]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of the product from step (i) (0.2 g), 2-trifluoromethylaniline (0.11 g) and N,N-diisopropylethylamine in 1,4-dioxane (5 ml) was heated at 80° C. for 18 hours. LC mass spectrum analysis showed cis-(3,5-dimethyl-4-(thieno[2,3-d]pyrimidin-4-yl)piperazin-1-yl]acetic acid present. PyBroP (0.18 g) and 4-dimethylaminopyridine (0.05 g) were added and the mixture further stirred at room temperature for 18 hours. The solvent was evaporated under reduced pressure and the residue purified by high pressure liquid chromatography (acetonitrile/0.1% aqueous ammonium acetate, gradient elution 25% to 75% organic phase) to give the title product as a white solid. Yield 0.08 g.

Workup

customThe solvent was evaporated under reduced pressure
customthe residue purified by high pressure liquid chromatography (acetonitrile/0.1% aqueous ammonium acetate, gradient elution 25% to 75% organic phase)

Sources & evidence

ORD record: ord-0afe86d16bfc4d82a959e255bfc07883
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06969713B2

Reaction notes

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