Trifluoroacetic acid methylene chloride → 2-Chloro-N-[(2R)-2,3-dihydroxy-propoxy]-3-(2-fluoro-4-iodo-phenylamino)-isonicotinamide

HRID 218915Notes

Reaction equation

HRID 218915 reaction equation
[Cl:1][C:2]1[C:3]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=2[F:28])=[C:4]([CH:17]=[CH:18][N:19]=1)[C:5]([NH:7][O:8][CH2:9][C@H:10]1[CH2:14][O:13]C(C)(C)[O:11]1)=[O:6].C(O)(C(F)(F)F)=O.ClCCl>>[Cl:1][C:2]1[C:3]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=2[F:28])=[C:4]([CH:17]=[CH:18][N:19]=1)[C:5]([NH:7][O:8][CH2:9][C@H:10]([OH:11])[CH2:14][OH:13])=[O:6]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 576496322-Chloro-N-{[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy}-3-(2-fluoro-4-iodo-phenylamino)-isonicotinamide

Product 1

HCID 576496352-Chloro-N-[(2R)-2,3-dihydroxy-propoxy]-3-(2-fluoro-4-iodo-phenylamino)-isonicotinamide

Procedure

Deprotection of 2-Chloro-N-{[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy}-3-(2-fluoro-4-iodo-phenylamino)-isonicotinamide with 50:50 mixture of TFA/dichloromethane at room temperature for 30 minutes afforded the desired product. Purification by reverse phase LC/MS [7.94 min; 482 (M+1)].

Sources & evidence

ORD record
ord-96b3cf2f3f2548d78245378325b140ba
Source dataset
uspto-grants-2012_06
Patent number
US08198457B2

Reaction notes

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