Water → 5-methyl-N-[6-(8-methyl-1,4-dioxaspiro[4.5]dec-8-yl)pyridin-3-yl]-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide

HRID 1748692Notes

Reaction equation

[CH3:1][C:2]1([C:12]2[N:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=2)[CH2:11][CH2:10][C:5]2([O:9][CH2:8][CH2:7][O:6]2)[CH2:4][CH2:3]1.[CH3:19][C:20]1[N:24]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][N:26]=2)[N:23]=[CH:22][C:21]=1[C:35](Cl)=[O:36].C(N(CC)CC)C.O>N1C=CC=CC=1>[CH3:19][C:20]1[N:24]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][N:26]=2)[N:23]=[CH:22][C:21]=1[C:35]([NH:18][C:15]1[CH:16]=[N:17][C:12]([C:2]2([CH3:1])[CH2:3][CH2:4][C:5]3([O:6][CH2:7][CH2:8][O:9]3)[CH2:10][CH2:11]2)=[CH:13][CH:14]=1)=[O:36]

Participants

Conditions

Temperature: 50 °C

Procedure

[6-(8-Methyl-1,4-dioxaspiro[4.5]dec-8-yl)pyridin-3-yl]amine (340 mg) was added to a solution of 5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxylic acid chloride (491 mg) described in Reference Example 180 in pyridine (7.0 ml) and stirred at 50° C. for an hour. After completion of the reaction, triethylamine (1.5 ml) and water was added and the precipitated solid was collected by filtration to give 5-methyl-N-[6-(8-methyl-1,4-dioxaspiro[4.5]dec-8-yl)pyridin-3-yl]-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide (618 mg) as a white solid.

Workup

additionwas added
filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record: ord-7de6985ebe1d49b796e7828e35fcfacb
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150555B2

Reaction notes

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