Ammonia → N-[(1R,2S)-1-[1-(4-fluorophenyl)indazol-5-yl]oxy-1-naphthalen-2-yl-propan-2-yl]-2-hydroxy-acetamide

HRID 1098790

Reaction equation

HRID 1098790 reaction equation
C([O:4][CH2:5][C:6](Cl)=[O:7])(=O)C.Cl.[F:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[C:25]3[C:20](=[CH:21][C:22]([O:26][C@H:27]([C:31]4[CH:40]=[CH:39][C:38]5[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=5)[CH:32]=4)[C@@H:28]([NH2:30])[CH3:29])=[CH:23][CH:24]=3)[CH:19]=[N:18]2)=[CH:13][CH:12]=1.C(N(CC)C(C)C)(C)C.N>C1COCC1.CO.O>[F:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[C:25]3[C:20](=[CH:21][C:22]([O:26][C@H:27]([C:31]4[CH:40]=[CH:39][C:38]5[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=5)[CH:32]=4)[C@@H:28]([NH:30][C:5](=[O:4])[CH2:6][OH:7])[CH3:29])=[CH:23][CH:24]=3)[CH:19]=[N:18]2)=[CH:13][CH:12]=1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 26297Acetoxyacetyl chlorideHCID 81531DiisopropylethylamineHCID 66812502(1R,2S)-1-(1-(4-fluorophenyl)-1H-indazol-5-yloxy)-1-(naphthalen-2-yl)propan-2-amine hydrochloride

Product 1

HCID 25013813N-[(1R,2S)-1-[1-(4-fluorophenyl)indazol-5-yl]oxy-1-naphthalen-2-yl-propan-2-yl]-2-hydroxy-acetamide

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Acetoxyacetyl chloride (13 μL, 0.12 mmol) was added to a stirred mixture of (1R,2S)-1-(1-(4-fluorophenyl)-1H-indazol-5-yloxy)-1-(naphthalen-2-yl)propan-2-amine hydrochloride (20a) (50 mg, 0.11 mmol) and N,N-diisopropylethylamine (60 μL, 0.34 mmol) in THF (2 mL). The reaction mixture was stirred at r.t. 45 min. Water (0.5 mL), 28% (aq) NH3 (0.5 mL) and MeOH (0.5 mL) was added to give a clear one-phase solution, the mixture was stirred over night at r.t.

Workup

  1. custom45 min
  2. customto give a clear one-phase solution
  3. stirringthe mixture was stirred over night at r.t.

Sources & evidence

ORD record
ord-2afddb4bbf67403fb1a84e272adf07b9
Source dataset
uspto-grants-2012_03
Patent number
US08143290B2

Linked notes

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