1-Hydroxybenzotriazole → (S)-5-chloro-N-(2'-methoxy-2-(2,2,2-trifluoroacetamido)-5H-spiro[oxazole-4,9'-xanthene]-7'-yl)picolinamide

HRID 1970311Notes

Reaction equation

HRID 1970311 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][C:8]([O:16][CH3:17])=[CH:9][CH:10]=3)[C@:5]3([CH2:21][O:20][C:19]([NH:22][C:23](=[O:28])[C:24]([F:27])([F:26])[F:25])=[N:18]3)[C:4]=2[CH:3]=1.[Cl:29][C:30]1[CH:31]=[CH:32][C:33]([C:36](O)=[O:37])=[N:34][CH:35]=1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>C(Cl)Cl.CN(C=O)C.O>[Cl:29][C:30]1[CH:31]=[CH:32][C:33]([C:36]([NH:1][C:2]2[CH:3]=[C:4]3[C:13]([O:12][C:11]4[CH:10]=[CH:9][C:8]([O:16][CH3:17])=[CH:7][C:6]=4[C@@:5]43[CH2:21][O:20][C:19]([NH:22][C:23](=[O:28])[C:24]([F:26])([F:25])[F:27])=[N:18]4)=[CH:14][CH:15]=2)=[O:37])=[N:34][CH:35]=1

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27628725-Chloro-2-picolinic acidHCID 86640720(S)-N-(2'-amino-7'-methoxy-5H-spiro[oxazole-4,9'-xanthene]-2-yl)-2,2,2-trifluoroacetamide

Product 1

HCID 86640719(S)-5-chloro-N-(2'-methoxy-2-(2,2,2-trifluoroacetamido)-5H-spiro[oxazole-4,9'-xanthene]-7'-yl)picolinamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

A 25 mL RBF containing a solution of (S)—N-(2′-amino-7′-methoxy-5H-spiro[oxazole-4,9′-xanthene]-2-yl)-2,2,2-trifluoroacetamide (0.058 g, 0.147 mmol), 5-chloropyridine-2-carboxylic acid (0.030 g, 0.190 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.045 g, 0.235 mmol) in DCM (4 mL) and DMF (0.25 mL) was treated with 1-hydroxy-1H-benzotriazole (0.014 g, 0.104 mmol) and stirred for 1.5 hrs at RT. The reaction was diluted with DCM (50 mL) and water (15 mL). The DCM layer was separated, dried over anhydrous sodium sulfate, and concentrated to dryness to yield (S)-5-chloro-N-(2′-methoxy-2-(2,2,2-trifluoroacetamido)-5H-spiro[oxazole-4,9′-xanthene]-7′-yl)picolinamide as a brownish solid. MS (ESI pos. ion) m/z: 533 (M+1).

Workup

  1. customThe DCM layer was separated
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-6a2c00154a3c4b01b359c35b1703783b
Source dataset
uspto-grants-2013_04
Patent number
US08426447B2

Reaction notes

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