Acetylglycine → HCID 59339784, compound

HRID 1098951Notes

Reaction equation

HRID 1098951 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][C@H:18]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=4)[C@@H:19]([NH2:21])[CH3:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[C:30]([NH:33][CH2:34][C:35](O)=[O:36])(=[O:32])[CH3:31].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C=O)C.CC#N.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][C@H:18]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=4)[C@@H:19]([NH:21][C:35]([CH2:34][NH:33][C:30](=[O:32])[CH3:31])=[O:36])[CH3:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 10972AcetylglycineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59339733(1R,2S)-1-(1-(4-fluorophenyl)indazol-5-yloxy)-1-(3-methoxyphenyl)propan-2-amine

Product 1

HCID 59339784HCID 59339784, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

(1R,2S)-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]oxy)-1-(3-methoxyphenyl)propan-2-amine (6a, 200 mg, 0.51 mmol) (1) and N-acetylglycine (59.8 mg, 0.51 mmol) were dissolved in dry DMF (2 ml). O-benzotriazol-1-yl-N,N,N′,N′-tetramethyl-uronium hexafluorophosphate (213 mg, 0.56 mmol) was added followed by N,N-diisopropylethylamine (270 μL, 1.53 mmol). The reaction was stirred at r.t. over night. The crude solution was diluted by MeCN/H2O and the product was purified on preparative HPLC.

Workup

  1. customthe product was purified on preparative HPLC

Sources & evidence

ORD record
ord-9e5235d16fc74d6ebc81e494f9ed14fa
Source dataset
uspto-grants-2012_03
Patent number
US08143290B2

Reaction notes

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