Trifluoroacetic acid methylene chloride → (S)-3-amino-N-(4-(3-aminopiperidin-1-yl)pyridin-3-yl)-6-(2-fluoro-5-isopentylphenyl)picolinamide

HRID 70002Notes

Reaction equation

HRID 70002 reaction equation
[NH2:1][C:2]1[C:3]([C:20]([NH:22][C:23]2[CH:24]=[N:25][CH:26]=[CH:27][C:28]=2[N:29]2[CH2:34][CH2:33][CH2:32][C@H:31]([NH:35]C(=O)OC(C)(C)C)[CH2:30]2)=[O:21])=[N:4][C:5]([C:8]2[CH:13]=[C:12](/[CH:14]=[CH:15]\[CH:16]([CH3:18])[CH3:17])[CH:11]=[CH:10][C:9]=2[F:19])=[CH:6][CH:7]=1.C(O)(C(F)(F)F)=O.C(Cl)Cl>>[NH2:1][C:2]1[C:3]([C:20]([NH:22][C:23]2[CH:24]=[N:25][CH:26]=[CH:27][C:28]=2[N:29]2[CH2:34][CH2:33][CH2:32][C@H:31]([NH2:35])[CH2:30]2)=[O:21])=[N:4][C:5]([C:8]2[CH:13]=[C:12]([CH2:14][CH2:15][CH:16]([CH3:17])[CH3:18])[CH:11]=[CH:10][C:9]=2[F:19])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 68161210HCID 68161210, compound

Product 1

HCID 68161348(S)-3-amino-N-(4-(3-aminopiperidin-1-yl)pyridin-3-yl)-6-(2-fluoro-5-isopentylphenyl)picolinamideYield 35%

Procedure

Method 2 of Example 49 was followed using (S,Z)-tert-butyl 1-(3-(3-amino-6-(2-fluoro-5-(3-methylbut-1-enyl)phenyl)picolinamido)pyridin-4-yl)piperidin-3-ylcarbamate which after Boc deprotection with 25% TFA/CH2Cl2 yielded (S)-3-amino-N-(4-(3-aminopiperidin-1-yl)pyridin-3-yl)-6-(2-fluoro-5-isopentylphenyl)picolinamide (35%). LCMS (m/z): 477.3 (MH+); LC Rt=2.91 min.

Sources & evidence

ORD record
ord-df75e686947945ec9b25e85f81c97aa0
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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