Ammonia → 3-(6-Methoxy-1,3-benzoxazol-2-yl)-5-[1-(1-methyl-4-piperidyl)pyrazol-4-yl]pyridin-2-amine

HRID 908412Notes

Reaction equation

[NH2:1][C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:12]=2[OH:19])=O)=[CH:6][C:5]([C:20]2[CH:21]=[N:22][N:23]([CH:25]3[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]3)[CH:24]=2)=[CH:4][N:3]=1.C(O)(C(F)(F)F)=O.N>C(O)(=O)C.CN(C=O)C>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]2[N:10]=[C:8]([C:7]3[C:2]([NH2:1])=[N:3][CH:4]=[C:5]([C:20]4[CH:21]=[N:22][N:23]([CH:25]5[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]5)[CH:24]=4)[CH:6]=3)[O:19][C:12]=2[CH:13]=1

Participants

Conditions

Temperature: 200 °C

Procedure

To a solution of 2-amino-N-(2-hydroxy-4-methoxy-phenyl)-5-[1-(1-methyl-4-piperidyl)pyrazol-4-yl]pyridine-3-carboxamide (110 mg) in acetic acid (1.8 ml) was added TFA (1.8 ml). The clear mixture was sealed into a microwave tube. The reaction was heated to 200° C. a 300 W microwave for 20 minutes. The solvents were evaporated. The residue was trituratred in diethyl ether, dried to give a yellow solid. The solid was dissolved in DMF (1.5 ml) and two drops of a 30% aqueous ammonia solution. The precipitate was filtered, washed with Ether and dried at 50° C. for 48 h to afford 3-(6-methoxy-1,3-benzoxazol-2-yl)-5-[1-(1-methyl-4-piperidyl)pyrazol-4-yl]pyridin-2-amine (25.00 mg). NMR Spectrum: (DMSOd6) 1.93-2.12 (m, 6H), 2.22 (s, 3H), 2.94-2.91 (m, 2H), 3.86 (s, 3H), 4.07-4.16 (m, 1H), 7.03 (dd, 1H), 7.40 (d, 1H), 7.57 (bs, 2H), 7.72 (d, 1H), 7.89 (d, 1H), 8.30 (s, 1H), 8.36 (d, 1H), 8.49 (d, 1H). Mass spectrum: M+H+ 405.

Workup

customThe clear mixture was sealed into a microwave tube
customThe solvents were evaporated
customdried
customto give a yellow solid
filtrationThe precipitate was filtered
washwashed with Ether
customdried at 50° C. for 48 h

Sources & evidence

ORD record: ord-5dd848eca1c94c67a6e1490e74649d7e
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017611B2

Reaction notes

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