2-(Trifluoromethyl)benzoyl chloride → HCID 67172005, compound

HRID 552163Notes

Reaction equation

[CH3:1][CH:2]([CH3:21])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[N:9]=[N:10][C:11]([N:14]2[CH2:19][CH2:18][CH:17]([NH2:20])[CH2:16][CH2:15]2)=[CH:12][CH:13]=1)=[O:7].C1(CCNC(C2N=NC(N3CC4C(C4N)C3)=CC=2)=O)CC1.[F:43][C:44]([F:55])([F:54])[C:45]1[CH:53]=[CH:52][CH:51]=[CH:50][C:46]=1[C:47](Cl)=[O:48]>>[CH3:1][CH:2]([CH3:21])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[N:9]=[N:10][C:11]([N:14]2[CH2:19][CH2:18][CH:17]([NH:20][C:47](=[O:48])[C:46]3[CH:50]=[CH:51][CH:52]=[CH:53][C:45]=3[C:44]([F:43])([F:54])[F:55])[CH2:16][CH2:15]2)=[CH:12][CH:13]=1)=[O:7]

Participants

Reactant 3

HCID 675612-(Trifluoromethyl)benzoyl chloride

HCID 11616280HCID 11616280, compound

HCID 67172284HCID 67172284, compound

Product 1

HCID 67172005HCID 67172005, compoundYield 29%

Procedure

Following the procedure as described in Example 4, making variations only as required to use 6-(4-aminopiperidin-1-yl)pyridazine-3-carboxylic acid (3-methylbutyl)amide to replace 6-(6-amino-3-azabicyclo[3.1.0]hex-3-yl)pyridazine-3-carboxylic acid (2-cyclopropylethyl)amide to react with 2-trifluoromethylbenzoyl chloride, the title compound was obtained as a white powder in 29% yield. 1H NMR (300 MHz, CDCl3) δ 8.00 (d, J=9.5 Hz, 1H), 7.85 (t, J=5.6 Hz, 1H), 7.70 (d, J=7.5 Hz, 1H), 7.52-7.61 (m, 3H), 7.01 (d, J=9.6 Hz, 1H), 5.71 (d, J=7.9 Hz, 1H), 4.49 (d, J=13.7 Hz, 2H), 4.30-4.38 (m, 1H), 3.49 (dd, J=6.6 and 13.7 Hz, 2H), 3.22-3.27 (m, 2H), 2.20-2.23 (m, 2H), 1.48-1.76 (m, 5H), 0.94 (d, J=6.6 Hz, 6H). MS (ES+) m/z 463.9 (M+1).

Sources & evidence

ORD record: ord-34f0afcdf766418eb793cb4af59b4e96
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07951805B2

Reaction notes

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