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 1098950Notes

Reaction equation

HRID 1098950 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-3460c74f080e412eb7238016359479ed
Source dataset
uspto-grants-2012_03
Patent number
US08143290B2

Reaction notes

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