Trifluoroacetic acid → ((3aS,5S,6aR)-5-aminohexahydro-2H-cyclopenta[b]furan-3a-yl)(3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)methanone

HRID 1747123Notes

Reaction equation

HRID 1747123 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[N:5][C:6]2[CH2:7][CH2:8][N:9]([C:13]([C@:15]34[CH2:22][C@H:21]([NH:23]C(=O)OC(C)(C)C)[CH2:20][C@H:16]3[O:17][CH2:18][CH2:19]4)=[O:14])[CH2:10][C:11]=2[CH:12]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:23][C@@H:21]1[CH2:20][C@H:16]2[O:17][CH2:18][CH2:19][C@@:15]2([C:13]([N:9]2[CH2:8][CH2:7][C:6]3[N:5]=[CH:4][C:3]([C:2]([F:32])([F:31])[F:1])=[CH:12][C:11]=3[CH2:10]2)=[O:14])[CH2:22]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86708132tert-butyl ((3aS,5S,6aR)-3a-(3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-6-carbonyl)hexahydro-2H-cyclopenta[b]furan-5-yl)carbamate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product of Step F (12.54 g, 24.8 mmol, 1 eq) in DCM (100 mL) at rt was added TFA (20 mL, 261 mmol, 10.6 eq). After 1 hr, the solution was concentrated. 3 M NaOH was added and the solution extracted with DCM, the organics combined, dried over MgSO4, and concentrated to afford the title compound of Step G. 1H NMR (CHLOROFORM-d) δ: 8.72 (s, 1H), 7.69 (br. s., 1H), 5.07 (d, J=4.9 Hz, 1H), 4.71-4.90 (m, 2H), 3.84-4.03 (m, 3H), 3.58-3.71 (m, 2H), 3.09-3.20 (m, 2H), 2.14-2.41 (m, 3H), 1.99-2.13 (m, 1H), 1.65-1.75 (m, 1H), 1.43-1.58 (m, 1H). Calculated for C17H20F3N3O2: 356.2 (M+1). found: 356.3.

Workup

  1. concentrationthe solution was concentrated
  2. addition3 M NaOH was added
  3. extractionthe solution extracted with DCM
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-93c6837d7c9944168d8d48e1be409dcb
Source dataset
uspto-grants-2015_10
Patent number
US09150532B2

Reaction notes

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