Trifluoroacetic acid → HCID 117667194, compound

HRID 712656Notes

Reaction equation

HRID 712656 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([O:7][CH2:8][C:9]2[CH:10]=[C:11]([C:15]3[CH:16]=[C:17]4[C:22](=[N:23][CH:24]=3)[NH:21][CH2:20][CH2:19][CH2:18]4)[CH:12]=[N:13][CH:14]=2)[CH2:3][CH2:2]1.FC(F)(F)[C:27]([OH:29])=[O:28]>C(Cl)Cl>[C:9]([O:29][C:27]([N:21]1[C:22]2[C:17](=[CH:16][C:15]([C:11]3[CH:12]=[N:13][CH:14]=[C:9]([CH2:8][O:7][CH:4]4[CH2:5][CH2:6][O:1][CH2:2][CH2:3]4)[CH:10]=3)=[CH:24][N:23]=2)[CH2:18][CH2:19][CH2:20]1)=[O:28])([CH3:10])([CH3:14])[CH3:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117667546HCID 117667546, compound

Product 1

HCID 117667194HCID 117667194, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-[5-(Tetrahydro-pyran-4-yloxymethyl)-pyridin-3-yl]-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester is synthesized according to the procedure of Suzuki Coupling Method IV, as illustrated above. It is then used to prepare 6-[5-(tetrahydro-pyran-4-yloxymethyl)-pyridin-3-yl]-1,2,3,4-tetrahydro-[1,8]naphthyridine according to the procedure for Step 2 of Example 27 using 20% trifluoroacetic acid in DCM as the reagent.

Sources & evidence

ORD record
ord-d6f9fb5ddb8e4653978b3096b903c044
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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