Trifluoroacetic acid → HCID 57687095, compound

HRID 908415Notes

Reaction equation

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

Participants

Conditions

Temperature: 200 °C

Procedure

To a solution of 2-amino-N-(2-hydroxy-3-methyl-phenyl)-5-[1-(1-methyl-4-piperidyl)pyrazol-4-yl]pyridine-3-carboxamide (80 mg) in acetic acid (1.3 ml) was added TFA (1.3 ml). The clear mixture was sealed into a microwave tube. The reaction was heated to 200° C. in a 300 W microwave for 20 minutes. The solvents were evaporated. The residue purified by preparative HPLC using a Waters X-Terra reverse-phase column and decreasingly polar mixtures of water (containing 1% acetic acid) and acetonitrile as eluent. The fractions containing the desired compound were evaporated to dryness to afford 3-(7-methyl-1,3-benzoxazol-2-yl)-5-[1-(1-methyl-4-piperidyl)pyrazol-4-yl]pyridin-2-amine (44.0 mg) NMR Spectrum: (DMSOd6) 1.94-2.10 (m, 6H), 2.22 (s, 3H), 2.62 (s, 3H), 2.84-2.92 (m, 2H), 4.09-4.17 (m, 1H), 7.27 (d, 1H), 7.32 (dd, 1H), 7.63 (bs, 2H), 7.64 (d, 1H), 7.93 (s, 1H), 8.30 (s, 1H), 8.44 (d, 1H), 8.52 (d, 1H); Mass spectrum: M+H+ 389.

Workup

customThe clear mixture was sealed into a microwave tube
customThe solvents were evaporated
customThe residue purified by preparative HPLC
additionThe fractions containing the desired compound
customwere evaporated to dryness

Sources & evidence

ORD record: ord-856343349b314ab68f3de21364f0e9bd
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017611B2

Reaction notes

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