Ammonia → HCID 58413146, compound

HRID 240616Notes

Reaction equation

HRID 240616 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]3[C:17]([CH3:18])=[C:16]([C:19](O)=[O:20])[S:15][C:11]=3[N:12]=[CH:13][N:14]=2)=[C:4]([O:22][C@H:23]2[CH2:28][CH2:27][CH2:26][N:25]([S:29]([CH3:32])(=[O:31])=[O:30])[CH2:24]2)[CH:3]=1.CC[N:35](C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.N>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]3[C:17]([CH3:18])=[C:16]([C:19]([NH2:35])=[O:20])[S:15][C:11]=3[N:12]=[CH:13][N:14]=2)=[C:4]([O:22][C@H:23]2[CH2:28][CH2:27][CH2:26][N:25]([S:29]([CH3:32])(=[O:30])=[O:31])[CH2:24]2)[CH:3]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58413207HCID 58413207, compound

Product 1

HCID 58413146HCID 58413146, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-[4-Fluoro-2-((S)-1-methanesulfonyl-piperidin-3-yloxy)-phenylamino]-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid (120 mg) at 0° C. was added DIPEA (49 μl) followed by HATU (104 mg) and the solution was stirred for 30 min. A solution of ammonia in methanol (7M; 0.3 ml) was added and the solution allowed to warm to room temperature and stirred for 1 h. The solvent was evaporated and traces of DMF removed by co-evaporation with toluene. The residue was triturated with MeOH and the solid collected by filtration to give the desired product.

Workup

  1. stirringstirred for 1 h
  2. customThe solvent was evaporated
  3. customtraces of DMF removed by co-evaporation with toluene
  4. customThe residue was triturated with MeOH
  5. filtrationthe solid collected by filtration

Sources & evidence

ORD record
ord-40727c1fba3d44cfb25aa3477b10cfb2
Source dataset
uspto-grants-2014_02
Patent number
US08648068B2

Reaction notes

Loading…