Diisopropylethylamine → HCID 56968093, compound

HRID 2365234Notes

Reaction equation

HRID 2365234 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](/[CH:13]=[CH:14]/[C:15]3[S:16][C:17]([C:21](O)=[O:22])=[C:18]([CH3:20])[N:19]=3)=[C:11]([CH3:24])[N:10]=[N:9]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.[NH2:56][CH:57]1[CH2:62][CH2:61][O:60][CH2:59][CH2:58]1>CN(C=O)C>[O:60]1[CH2:61][CH2:62][CH:57]([NH:56][C:21]([C:17]2[S:16][C:15](/[CH:14]=[CH:13]/[C:12]3[N:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)[N:9]=[N:10][C:11]=3[CH3:24])=[N:19][C:18]=2[CH3:20])=[O:22])[CH2:58][CH2:59]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 4192234-AminotetrahydropyranHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67496330HCID 67496330, compound

Product 1

HCID 56968093HCID 56968093, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-{(E)-2-[3-(4-fluoro-phenyl)-5-methyl-3H-[1,2,3]triazol-4-yl]-vinyl}-4-methyl-thiazole-5-carboxylic acid (72 mg, 0.21 mmol) and TBTU (74 mg, 0.23 mmol) in DMF (3 mL) was added DIPEA (178 μL, 1.05 mmol). Then 4-aminotetrahydropyran (23 mg, 0.23 mmol) was added and the mixture was stirred at room temperature under Ar for 2 h. The mixture was then evaporated and purification by chromatography (silica, 30 to 80% ethylacetate in heptane) afforded the title compound (68 mg, 76%) as a light yellow solid. MS: m/e=428.3 [M+H]+.

Workup

  1. customThe mixture was then evaporated
  2. custompurification by chromatography (silica, 30 to 80% ethylacetate in heptane)

Sources & evidence

ORD record
ord-59a39dc08dea4d9dbf521d46161c8310
Source dataset
uspto-grants-2014_04
Patent number
US08697696B2

Reaction notes

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