Trifluoroacetate → HCID 178464317, compound

HRID 2274416Notes

Reaction equation

[CH2:1]([N:3]([CH2:41][CH3:42])[C:4](=[O:40])[NH:5][C:6]1[C:7]([C:17]2[NH:18][C:19]3[CH:25]=[C:24]([N:26]([CH2:34][CH2:35][N:36]([CH3:38])[CH3:37])[C:27]([N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])=[O:28])[C:23]([F:39])=[CH:22][C:20]=3[N:21]=2)=[N:8][N:9](C2CCCCO2)[CH:10]=1)[CH3:2].FC(F)(F)C([O-])=O>>[CH2:41]([N:3]([CH2:1][CH3:2])[C:4](=[O:40])[NH:5][C:6]1[C:7]([C:17]2[NH:18][C:19]3[CH:25]=[C:24]([N:26]([CH2:34][CH2:35][N:36]([CH3:38])[CH3:37])[C:27]([N:29]([CH2:30][CH3:31])[CH2:32][CH3:33])=[O:28])[C:23]([F:39])=[CH:22][C:20]=3[N:21]=2)=[N:8][NH:9][CH:10]=1)[CH3:42]

Participants

Reactant 2

HCID 84468Trifluoroacetate

HCID 178464306HCID 178464306, compound

Product 1

HCID 178464317HCID 178464317, compoundYield 63.1%

Procedure

In the same manner as for step V1 of example 15 (see below), 100 mg of 1-{2-[4-(3,3-diethylureido)-1-(tetrahydropyran-2-yl)-1H-pyrazol-3-yl]-6-fluoro-3H-benzimidazol-5-yl}-1-(2-dimethylaminoethyl)-3,3-diethylurea (stage 5, example 15) are deprotected, and 54 mg of 1-{2-[4-(3,3-diethylureido)-1H-pyrazol-3-yl]-6-fluoro-3H-benzimidazol-5-yl}-1-(2-dimethylaminoethyl)-3,3-diethylurea are isolated in the form of a trifluoroacetate salt. 1H NMR (300 MHz, DMSO-d6, δ in ppm), for this batch, we observe a 60%-40% resolution of tautomers with: 0.75 (m, 6H); 1.22 (m, 6H); from 2.30 to 2.86 (broad m partially masked, 8H); 3.02 (q, J=7.0 Hz, 4H); 3.42 (q, J=7.0 Hz, 4H); 3.64 (broad m, 2H); 7.36 (m, 1H); 7.52 (m, 1H); 8.02 (s, 1H); 9.35 (broad m, 1H); 9.71 (s, 0.4H); 9.74 (s, 0.6H); 13.1 (broad s, 1H); 13.15 (broad s, 0.4H); 13.2 (broad s, 0.6H). ES mass spectrum: 502(+)=(M+H)(+)

Sources & evidence

ORD record: ord-65e3d020698a4b079accd4ba4c78ba24
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126969B2

Reaction notes

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