Trifluoroacetic acid → HCID 58988002, compound

HRID 2241428Notes

Reaction equation

COC1C=CC(C[N:8]2[C:12]3=[N:13][CH:14]=[CH:15][C:16]([O:17][C:18]4[CH:23]=[CH:22][C:21]([NH:24][C:25]([C:27]5[C:28](=[O:40])[N:29]([C:33]6[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=6)[N:30]=[CH:31][CH:32]=5)=[O:26])=[CH:20][C:19]=4[F:41])=[C:11]3[C:10]([NH:42][C@H:43]3[CH2:48][CH2:47][N:46]([CH2:49][CH3:50])[CH2:45][C@H:44]3[F:51])=[N:9]2)=CC=1.FC(F)(F)C(O)=O>>[CH2:49]([N:46]1[CH2:47][CH2:48][C@H:43]([NH:42][C:10]2[C:11]3[C:12](=[N:13][CH:14]=[CH:15][C:16]=3[O:17][C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25]([C:27]4[C:28](=[O:40])[N:29]([C:33]5[CH:34]=[CH:35][C:36]([F:39])=[CH:37][CH:38]=5)[N:30]=[CH:31][CH:32]=4)=[O:26])=[CH:20][C:19]=3[F:41])[NH:8][N:9]=2)[C@H:44]([F:51])[CH2:45]1)[CH3:50]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 68512105HCID 68512105, compound

Product 1

HCID 58988002HCID 58988002, compoundYield 66.2%

Procedure

Prepared from ±N-(4-(1-(4-methoxybenzyl)-3-((3R*,4S*)-1-ethyl-3-fluoropiperidin-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorophenyl)-2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxamide (8 mg, 0.01 mmol) and 2,2,2-trifluoroacetic acid (0.43 mL, 5.5 mmol) according to the procedure described for Example 145, Step C. The product was obtained as a pale yellow powder (4 mg, 51%). HPLC: 95% purity (220 nm); LRMS (ESI+): 97% purity, 220 nm, m/z 605 (M+1) detected; 1H NMR (400 MHz, MeOD-d3) δ 11.98 (s, 1H), 8.35 (m, 3H), 8.09 (d, J=13 Hz, 1H), 7.67 (m, 2H), 7.53 (m, 2H), 7.29 (t, J=9 Hz, 2H), 6.42 (d, J=5 Hz, 1H), 5.37 (d, J=47 Hz, 1H), 4.26 (m, 1H), 3.97 (m, 1H), 3.66 (m, 1H), 3.52 (m, 1H), 3.28 (m, 2H), 2.34 (m, 2H), 1.39 (t, J=7 Hz, 3H).

Sources & evidence

ORD record: ord-0e5b8ca1508c4056b0199a1976b41dfb
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723330B2

Reaction notes

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