Hydrochloric Acid → (R)-(1-(5,6-Diaminopyridin-2-yl)piperidin-3-yl)(3,3-difluoropyrrolidin-1-yl)methanone dihydrochloride

HRID 931095Notes

Reaction equation

HRID 931095 reaction equation
[ClH:1].Cl.[NH2:3][C:4]1[CH:5]=[CH:6][C:7]([N:11]2[CH2:16][CH2:15][CH2:14][C@@H:13]([C:17](N3CCCC3)=[O:18])[CH2:12]2)=[N:8][C:9]=1[NH2:10].[F:24][C:25]1([F:30])[CH2:29][CH2:28][NH:27][CH2:26]1.Cl>CO>[ClH:1].[ClH:1].[NH2:3][C:4]1[CH:5]=[CH:6][C:7]([N:11]2[CH2:16][CH2:15][CH2:14][C@@H:13]([C:17]([N:27]3[CH2:28][CH2:29][C:25]([F:30])([F:24])[CH2:26]3)=[O:18])[CH2:12]2)=[N:8][C:9]=1[NH2:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 27828273,3-DifluoropyrrolidineHCID 89854051(R)-(1-(5,6-Diaminopyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone dihydrochloride

Product 1

HCID 117966390(R)-(1-(5,6-Diaminopyridin-2-yl)piperidin-3-yl)(3,3-difluoropyrrolidin-1-yl)methanone dihydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared by a method analogous to the one used for Intermediate 1, but using 3,3-difluoropyrrolidine instead of pyrrolidine for Step 1 and a solution of hydrogen chloride in methanol (1.25 M) for Step 2. MS (ES+) (M+H) 326.1; LCMS retention time: 0.26 minutes (Method M). 1H NMR (DMSO, 400 MHz): δ 1.45-1.62 (m, 2H), 1.65-1.72 (m, 1H), 1.82-1.90 (m, 1H), 2.30-2.45 (m, 2H), 2.76-2.91 (m, 2H), 3.46-3.54 (m, 1H), 3.64-3.78 (m, 2H), 3.84-3.92 (m, 1H), 3.95-4.04 (m, 2H), 4.06-4.13 (m, 1H), 4.13-4.62 (m, 6H), 6.14 (d, 1H), 7.24 (d, 1H).

Sources & evidence

ORD record
ord-ef4ddf3d605b44caac37506cba5d362c
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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