Sulfuric Acid → (S)-((S)-1-(4-(3-fluoro-4-(7-methoxyquinolin-4-yloxy)phenylcarbamoyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydropyrazol-1-yl)propan-2-yl)2-aminopropanoate sulfate

HRID 1517821Notes

Reaction equation

[NH2:1][C@@H:2]([CH3:45])[C:3]([O:5][C@@H:6]([CH3:44])[CH2:7][N:8]1[C:12]([CH3:13])=[C:11]([C:14](=[O:36])[NH:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]3[C:32]4[C:27](=[CH:28][C:29]([O:33][CH3:34])=[CH:30][CH:31]=4)[N:26]=[CH:25][CH:24]=3)=[C:18]([F:35])[CH:17]=2)[C:10](=[O:37])[N:9]1[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:4].[OH:46][S:47]([OH:50])(=[O:49])=[O:48]>>[S:47]([OH:50])([OH:49])(=[O:48])=[O:46].[F:35][C:18]1[CH:17]=[C:16]([NH:15][C:14]([C:11]2[C:10](=[O:37])[N:9]([C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)[N:8]([CH2:7][C@@H:6]([O:5][C:3](=[O:4])[C@@H:2]([NH2:1])[CH3:45])[CH3:44])[C:12]=2[CH3:13])=[O:36])[CH:21]=[CH:20][C:19]=1[O:22][C:23]1[C:32]2[C:27](=[CH:28][C:29]([O:33][CH3:34])=[CH:30][CH:31]=2)[N:26]=[CH:25][CH:24]=1

Participants

Reactant 2

HCID 1118Sulfuric Acid

HCID 59491006(S)-((S)-1-(4-(3-fluoro-4-(7-methoxyquinolin-4-yloxy)phenylcarbamoyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydropyrazol-1-yl)propan-2-yl)2-aminopropanoate

Product 1

HCID 66669832(S)-((S)-1-(4-(3-fluoro-4-(7-methoxyquinolin-4-yloxy)phenylcarbamoyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydropyrazol-1-yl)propan-2-yl)2-aminopropanoate sulfate

Procedure

The title compound was prepared according to the procedure described in Example 13 Step 3 by using (2S)—(S)-1-(4-(4-(7-methoxyquinolin-4-yloxy)-3-fluorophenyl-carbamoyl)-2,3-dihydro-5-methyl-3-oxo-2-phenylpyrazol-1-yl)propan-2-yl 2-aminopropanoate (61.3 mg, 0.1 mmol) and H2SO4 (1 mL, 0.1 mol/L, Shantou Xilong Chemical Factory). The title compound was obtained as a yellow solid (61.5 mg, 86.5%).

Workup

customThe title compound was prepared

Sources & evidence

ORD record: ord-3b7644bc1018412a820e1dc7430bf9a8
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232294B2

Reaction notes

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