Trifluoroacetic acid → HCID 69481068, compound

HRID 2364348Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:26])=[C:14]([C:21](OCC)=[O:22])[C:15](=[O:20])[N:16]3[CH3:19])=[N:11][CH:10]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:34][S:35]([N:38]1[CH2:43][CH2:42][CH:41]([NH2:44])[CH2:40][CH2:39]1)(=[O:37])=[O:36].FC(F)(F)C(O)=O>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:26])=[C:14]([C:21]([NH:44][CH:41]4[CH2:42][CH2:43][N:38]([S:35]([CH3:34])(=[O:37])=[O:36])[CH2:39][CH2:40]4)=[O:22])[C:15](=[O:20])[N:16]3[CH3:19])=[N:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

Reactant 4

HCID 6422Trifluoroacetic acid

HCID 8471Triethylamine

HCID 113558261-(Methanesulfonyl)piperidin-4-amine

HCID 54730000Ethyl 7-[(4-Fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 69481068HCID 69481068, compoundYield 43%

Procedure

In a similar manner to that described in example 196, from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (30 mg, 0.084 mmol) described in example 92, triethylamine (0.1 mL, 0.818 mmol), and 1-(methylsulfonyl)-4-piperidinamine as the trifluoroacetic acid salt (171 mg, 0.589 mmol), was prepared 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-N-[-(methylsulfonyl)-4-piperidinyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (15 mg, 43% yield), as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.33 (d, J=7.6 Hz, 1 H), 8.58 (s, 1 H), 7.41 (s, 1 H), 7.18-7.14 (m, 2 H), 7.05-7.00 (m, 2 H), 4.14-4.09 (m, 3 H), 3.75-3.69 (m, 2 H), 3.58 (s, 3 H), 2.97 (m, 2 H), 2.82 (s, 3 H), 2.14 (m, 2 H), 1.76 (m, 2 H); HRMS m/z calcd for C23H26FN4O5S: 489.1602. Found: 489.1609.

Sources & evidence

ORD record: ord-ebef3f93068a490389653d0db4406d5a
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691991B2

Reaction notes

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