Diisopropylethylamine → HCID 57329775, compound

HRID 2365215Notes

Reaction equation

HRID 2365215 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[N:11][N:10]([CH3:13])[C:9]=2[CH2:14][O:15][C:16]2[CH:20]=[C:19]([C:21]([OH:23])=O)[O:18][N:17]=2)=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:55][CH:56]1[CH2:61][CH2:60][O:59][CH2:58][CH2:57]1>CN(C=O)C>[O:59]1[CH2:60][CH2:61][CH:56]([NH:55][C:21]([C:19]2[O:18][N:17]=[C:16]([O:15][CH2:14][C:9]3[N:10]([CH3:13])[N:11]=[N:12][C:8]=3[C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH:20]=2)=[O:23])[CH2:57][CH2:58]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 4192234-AminotetrahydropyranHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67496157HCID 67496157, compound

Product 1

HCID 57329775HCID 57329775, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-[5-(4-fluoro-phenyl)-3-methyl-3H-[1,2,3]triazol-4-ylmethoxy]-isoxazole-5-carboxylic acid (40 mg, 0.13 mmol) and TBTU (64.6 mg, 0.20 mmol) in DMF (2.0 mL) was added DIPEA (106.9 μL, 0.63 mmol). Then 4-aminotetrahydropyran (14 mg, 0.14 mmol) was added and the mixture was stirred at room temperature under Ar for 1 h. The mixture was then evaporated and purification by chromatography (silica, 50 to 100% ethyl acetate in heptane) afforded the title compound (35 mg, 70%) as a white solid. MS: m/e=402.2 [M+H]+.

Workup

  1. customThe mixture was then evaporated
  2. custompurification by chromatography (silica, 50 to 100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-637e2c36427f426197ca8664cc96bba5
Source dataset
uspto-grants-2014_04
Patent number
US08697696B2

Reaction notes

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