Diisopropylethylamine → N-[(1R,2S)-1-(3,4-dimethylphenyl)-1-[1-(4-fluorophenyl)indazol-5-yl]oxy-propan-2-yl]-5-methyl-1,3-thiazole-2-carboxamide

HRID 13189Notes

Reaction equation

HRID 13189 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[N:4][CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH3:43][C:44]1[CH:45]=[C:46]([C@@H:51]([O:55][C:56]2[CH:57]=[C:58]3[C:62](=[CH:63][CH:64]=2)[N:61]([C:65]2[CH:70]=[CH:69][C:68]([F:71])=[CH:67][CH:66]=2)[N:60]=[CH:59]3)[C@@H:52]([NH2:54])[CH3:53])[CH:47]=[CH:48][C:49]=1[CH3:50]>CN1C(=O)CCC1>[CH3:43][C:44]1[CH:45]=[C:46]([C@@H:51]([O:55][C:56]2[CH:57]=[C:58]3[C:62](=[CH:63][CH:64]=2)[N:61]([C:65]2[CH:66]=[CH:67][C:68]([F:71])=[CH:69][CH:70]=2)[N:60]=[CH:59]3)[C@@H:52]([NH:54][C:7]([C:5]2[S:6][C:2]([CH3:1])=[CH:3][N:4]=2)=[O:9])[CH3:53])[CH:47]=[CH:48][C:49]=1[CH3:50]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 218773495-Methyl-1,3-thiazole-2-carboxylic acidHCID 66812804HCID 66812804, compound

Product 1

HCID 59339819N-[(1R,2S)-1-(3,4-dimethylphenyl)-1-[1-(4-fluorophenyl)indazol-5-yl]oxy-propan-2-yl]-5-methyl-1,3-thiazole-2-carboxamide

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

5-methyl-1,3-thiazole-2-carboxylic acid (29 mg, 0.2 mmol) was dissolved in NMP (1 mL) together with HATU (76 mg, 0.2 mmol) and DIEA (133 uL, 0.8 mmol). The mixture was stirred in r.t. for 5 min before (1R,2S)-1-(3,4-dimethylphenyl)-1-(1-(4-fluorophenyl)-1H-indazol-5-yloxy)propan-2-amine (58 mg, 0.15 mmol, prepared analogously to Example 6a with corresponding starting material) was added. The reaction mixture was stirred in r.t. overnight before it was evaporated under reduced pressure and purified by semi-prep. HPLC.

Workup

  1. customprepared analogously to Example 6a with corresponding starting material)
  2. additionwas added
  3. customwas evaporated under reduced pressure
  4. custompurified by semi-prep

Sources & evidence

ORD record
ord-d464423b125044da8164bd05c0f95ef2
Source dataset
uspto-grants-2010_06
Patent number
US07728030B2

Reaction notes

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