Tetrahydro-4H-pyran-4-one → ((3aS,5S,6aR)-5-((tetrahydro-2H-pyran-4-yl)amino)hexahydro-2H-cyclopenta[b]furan-3a-yl)(3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)methanone

HRID 1747124Notes

Reaction equation

HRID 1747124 reaction equation
[NH2:1][C@@H:2]1[CH2:9][C@H:5]2[O:6][CH2:7][CH2:8][C@@:4]2([C:10]([N:12]2[CH2:21][CH2:20][C:19]3[N:18]=[CH:17][C:16]([C:22]([F:25])([F:24])[F:23])=[CH:15][C:14]=3[CH2:13]2)=[O:11])[CH2:3]1.[O:26]1[CH2:31][CH2:30][C:29](=O)[CH2:28][CH2:27]1>>[O:26]1[CH2:31][CH2:30][CH:29]([NH:1][C@@H:2]2[CH2:9][C@H:5]3[O:6][CH2:7][CH2:8][C@@:4]3([C:10]([N:12]3[CH2:21][CH2:20][C:19]4[N:18]=[CH:17][C:16]([C:22]([F:25])([F:24])[F:23])=[CH:15][C:14]=4[CH2:13]3)=[O:11])[CH2:3]2)[CH2:28][CH2:27]1

Participants

3

Reactant 2

HCID 121599Tetrahydro-4H-pyran-4-oneHCID 86708133((3aS,5S,6aR)-5-aminohexahydro-2H-cyclopenta[b]furan-3a-yl)(3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)methanone

Product 1

HCID 71768721((3aS,5S,6aR)-5-((tetrahydro-2H-pyran-4-yl)amino)hexahydro-2H-cyclopenta[b]furan-3a-yl)(3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)methanone

Procedure

The title compound was prepared from reaction of the product of Example 1, Step G and tetrahydro-4H-pyran-4-one following the procedure described in Example 1, Step H. 1H NMR (CHLOROFORM-d) δ: 8.72 (br. s., 1H), 7.70 (br. s., 1H), 5.04 (d, J=4.6 Hz, 1H), 4.78 (br. s., 2H), 3.95 (s, 2H), 3.97 (s, 3H), 3.53-3.75 (m, 2H), 3.28-3.49 (m, 2H), 3.14 (br. s., 2H), 2.62-2.81 (m, 1H), 2.29 (dd, J=12.8, 5.5 Hz, 3H), 1.99-2.17 (m, 1H), 1.60-1.92 (m, 3H), 1.18-1.57 (m, 5H). Calculated for C22H28F3N3O3: 440.2 (M+1). found: 440.2.

Sources & evidence

ORD record
ord-1fb08caf740d48e79e312475d6420567
Source dataset
uspto-grants-2015_10
Patent number
US09150532B2

Reaction notes

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