Trifluoroacetic acid → N-((trans-2-aminocyclohexyl)methyl)-2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-amine

HRID 526937Notes

Reaction equation

HRID 526937 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15]([NH:17][CH2:18][C@@H:19]4[CH2:24][CH2:23][CH2:22][CH2:21][C@H:20]4[NH:25]C(=O)OC(C)(C)C)[C:14]([F:33])=[CH:13][N:12]=3)=[CH:9][N:8]([S:34]([C:37]3[CH:43]=[CH:42][C:40]([CH3:41])=[CH:39][CH:38]=3)(=[O:36])=[O:35])[C:5]2=[N:6][CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:25][C@@H:20]1[CH2:21][CH2:22][CH2:23][CH2:24][C@H:19]1[CH2:18][NH:17][C:15]1[C:14]([F:33])=[CH:13][N:12]=[C:11]([C:10]2[C:4]3[C:5](=[N:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)[N:8]([S:34]([C:37]3[CH:38]=[CH:39][C:40]([CH3:41])=[CH:42][CH:43]=3)(=[O:36])=[O:35])[CH:9]=2)[N:16]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68007592tert-butyl trans-2-((2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)methyl)cyclohexylcarbamate2×

Product 1

HCID 68007392N-((trans-2-aminocyclohexyl)methyl)-2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the tert-butyl trans-2-((2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)methyl)cyclohexylcarbamate, 14e, (0.52 g) in CH2Cl2 (5 mL) was treated with TFA (2.5 mL) for 30 min. the solution was concentrated in vacuo and the resulting crude material was taken up in CH3CN and concentrated in vacuo several times to remove excess TFA and to provide the desired amine, 14f, as racemic mixture of trans isomers, as the TFA salt, which was sufficiently pure for use in the next reaction.

Workup

  1. concentrationwas concentrated in vacuo
  2. concentrationconcentrated in vacuo several times
  3. customto remove excess TFA

Sources & evidence

ORD record
ord-b82b43e0223345d7a76c47f52628d3ea
Source dataset
uspto-grants-2016_05
Patent number
US09345708B2

Reaction notes

Loading…