Trifluoroacetic acid → N-{7-[4-((1R,2S)-2-Amino-3-fluoro-1-hydroxy-propyl)-phenyl]-imidazo[1,2-a]pyridin-2-ylmethyl}-methanesulfonamide

HRID 525558Notes

Reaction equation

HRID 525558 reaction equation
C(OC([N:8]1[C@H:12]([CH2:13][F:14])[C@@H:11]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][N:24]4[CH:27]=[C:28]([CH2:30][NH:31][S:32]([CH3:35])(=[O:34])=[O:33])[N:29]=[C:23]4[CH:22]=3)=[CH:17][CH:16]=2)[O:10]C1(C)C)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:8][C@H:12]([CH2:13][F:14])[C@@H:11]([C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][N:24]3[CH:27]=[C:28]([CH2:30][NH:31][S:32]([CH3:35])(=[O:33])=[O:34])[N:29]=[C:23]3[CH:22]=2)=[CH:17][CH:16]=1)[OH:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86695442(4S,5R)-4-Fluoromethyl-5-{4-[2-(methanesulfonylamino-methyl)-imidazo[1,2-a]pyridin-7-yl]-phenyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Product 1

HCID 86695443N-{7-[4-((1R,2S)-2-Amino-3-fluoro-1-hydroxy-propyl)-phenyl]-imidazo[1,2-a]pyridin-2-ylmethyl}-methanesulfonamideYield 160.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (4S,5R)-4-Fluoromethyl-5-{4-[2-(methanesulfonylamino-methyl)-imidazo[1,2-a]pyridin-7-yl]-phenyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (75 mg, 0.14 mmol) in CH2Cl2 (1 mL) is added trifluoroacetic acid (0.3 mL) drop wise at 0° C. then stirred at room temperature for 2 hours. The reaction mixture is concentrated and stripped with CH2Cl2 to afford title compound (88 mg, crude) which is used as is in the next step. LC-MS (m/z): [M+H]=393.1.

Workup

  1. concentrationThe reaction mixture is concentrated

Sources & evidence

ORD record
ord-086f616cd5c04597b0a3baa9d1f91aea
Source dataset
uspto-grants-2016_05
Patent number
US09340564B2

Reaction notes

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