2-(Trifluoromethyl)benzoyl chloride → HCID 67172311, compound

HRID 552164Notes

Reaction equation

[CH3:1][CH:2]([CH3:20])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[N:9]=[N:10][C:11]([N:14]2[CH2:18][CH2:17][CH:16]([NH2:19])[CH2:15]2)=[CH:12][CH:13]=1)=[O:7].C1(CCNC(C2N=NC(N3CC4C(C4N)C3)=CC=2)=O)CC1.[F:42][C:43]([F:54])([F:53])[C:44]1[CH:52]=[CH:51][CH:50]=[CH:49][C:45]=1[C:46](Cl)=[O:47]>>[CH3:1][CH:2]([CH3:20])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[N:9]=[N:10][C:11]([N:14]2[CH2:18][CH2:17][CH:16]([NH:19][C:46](=[O:47])[C:45]3[CH:49]=[CH:50][CH:51]=[CH:52][C:44]=3[C:43]([F:42])([F:53])[F:54])[CH2:15]2)=[CH:12][CH:13]=1)=[O:7]

Participants

Reactant 3

HCID 675612-(Trifluoromethyl)benzoyl chloride

HCID 67172284HCID 67172284, compound

HCID 67172413HCID 67172413, compound

Product 1

HCID 67172311HCID 67172311, compoundYield 99%

Procedure

Following the procedure as described in Example 4, making variations only as required to use 6-(3-aminopyrrolidin-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 99% yield. 1H NMR (300 MHz, CDCl3) δ 7.99 (d, J=9.3 Hz, 1H), 7.85 (t, J=5.6 Hz, 1H), 7.69 (d, J=7.7 Hz, 1H), 7.52-7.61 (m, 3H), 6.72 (d, J=9.4 Hz, 1H), 6.07 (d, J=7.0 Hz, 1H), 4.86-4.89 (m, 1H), 3.94-3.97 (m, 1H), 3.64-3.73 (m, 3H), 3.47 (dd, J=6.7 and 13.6 Hz, 2H), 2.42-2.49 (m, 1H), 2.20-2.26 (m, 1H), 1.64-1.75 (m, 1H), 1.47-1.51 (m, 2H), 0.93 (d, J=6.7 Hz, 6H). MS (ES+) m/z 450.4 (M+1).

Sources & evidence

ORD record: ord-f815a36914ab4ccea2c2bd467b1c65cf
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07951805B2

Reaction notes

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