Isopropylamine → HCID 57329858, compound

HRID 2365231Notes

Reaction equation

HRID 2365231 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/[CH:14]=[CH:15]/[C:16]2[S:17][C:18]([C:22](O)=[O:23])=[C:19]([CH3:21])[N:20]=2)=[CH:4][CH:3]=1.CN(C(O[N:33]1N=N[C:35]2C=CC=[CH:39][C:34]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.C(N)(C)C>CN(C=O)C>[CH:34]([NH:33][C:22]([C:18]1[S:17][C:16](/[CH:15]=[CH:14]/[C:9]2[N:10]([CH3:13])[N:11]=[N:12][C:8]=2[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[N:20][C:19]=1[CH3:21])=[O:23])([CH3:39])[CH3:35]

Participants

6

Reactant 4

HCID 6363IsopropylamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67497106HCID 67497106, compound

Product 1

HCID 57329858HCID 57329858, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-{(E)-2-[5-(4-fluoro-phenyl)-3-methyl-3H-[1,2,3]triazol-4-yl]-vinyl}-4-methyl-thiazole-5-carboxylic acid (75 mg, 0.22 mmol) and TBTU (77 mg, 0.24 mmol) in DMF (0.4 mL) was added DIPEA (186 μL, 1.09 mmol). Then isopropylamine (21 μL, 0.24 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, 1 to 5% methanol in dichloromethane) afforded the title compound (28 mg, 33%) as an off white solid after recrystallisation from ethylacetate and heptane. MS: m/e=386.4 [M+H]+.

Workup

  1. customThe mixture was then evaporated
  2. custompurification by chromatography (silica, 1 to 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-1b9c7805a8d548cf863abd54f4a3a5d0
Source dataset
uspto-grants-2014_04
Patent number
US08697696B2

Reaction notes

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