Trifluoroacetic acid → HCID 57657636, compound

HRID 1514394Notes

Reaction equation

[CH3:1][C@H:2]1[N:7]([C:8]2[C:9]3[N:23]=[CH:22][CH:21]=[CH:20][C:10]=3[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:12][N:13]=2)[CH2:6][CH2:5][N:4](C(OC(C)(C)C)=O)[CH2:3]1.FC(F)(F)C(O)=O>>[CH3:1][C@@H:2]1[CH2:3][NH:4][CH2:5][CH2:6][N:7]1[C:8]1[C:9]2[N:23]=[CH:22][CH:21]=[CH:20][C:10]=2[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:12][N:13]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 57657604HCID 57657604, compound

Product 1

HCID 57657636HCID 57657636, compoundYield 98.1%

Procedure

Using methods described in Example 6, and starting with (R)-tert-butyl 3-methyl-4-(5-phenylpyrido[3,2-d]pyridazin-8-yl)piperazine-1-carboxylate 74 (325 mg, 801 μmol) and trifluoroacetic acid (3.09 ml, 40.1 mmol), yielded (R)-8-(2-methylpiperazin-1-yl)-5-phenylpyrido[3,2-d]pyridazine 75 (240 mg, 98.1% yield). 1H-NMR (400 MHz, CDCl3): δ 9.07 (dd, J=4.3, 2.0 Hz, 1H), 8.31 (dd, J=8.6, 2.0 Hz, 1H), 7.72 (m, 2H), 7.64 (dd, J=8.6, 4.3 Hz, 1H), 7.52 (m, 3H), 5.38 (m, 1H), 4.60 (dt, J=13.3, 2.3 Hz, 1H), 3.64 (ddd, J=13.7, 10.6, 4.7 Hz, 1H), 3.31 (dd, J=12.5, 3.9 Hz, 1H), 3.15 (m, 2H), 2.95 (dd, J=12.5, 1.6 Hz, 1H), 1.43 (d, J=7.0 Hz, 1H). MS 305.2 306.1 (M+H, found).

Sources & evidence

ORD record: ord-3df977e96b3f4a2a83f3008959dea598
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222251B2

Reaction notes

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