Isopropylamine → HCID 57378560, compound

HRID 1258881Notes

Reaction equation

HRID 1258881 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[C:14]2[N:15]=[CH:16][N:17]([C:19]3[CH:27]=[CH:26][C:22]([C:23]([OH:25])=O)=[CH:21][CH:20]=3)[CH:18]=2)=[CH:4][CH:3]=1.CN(C(O[N:36]1N=N[C:38]2C=CC=[CH:42][C:37]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>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]=[N:11][N:10]([CH3:13])[C:9]=2[C:14]2[N:15]=[CH:16][N:17]([C:19]3[CH:27]=[CH:26][C:22]([C:23]([NH:36][CH:37]([CH3:42])[CH3:38])=[O:25])=[CH:21][CH:20]=3)[CH:18]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6363IsopropylamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67954954HCID 67954954, compound

Product 1

HCID 57378560HCID 57378560, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-{4-[5-(4-fluoro-phenyl)-3-methyl-3H-[1,2,3]triazol-4-yl]-imidazol-1-yl}-benzoic acid (75 mg, 0.21 mmol) and TBTU (73 mg, 0.23 mmol) in DMF (0.8 mL) was added DIPEA (177 μL, 1.03 mmol). Then isopropylamine (19 μL, 0.23 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, 0 to 100% ethyl acetate in heptane, then 0 to 10% methanol in dichloromethane) afforded the title compound (57 mg, 68%) as a white solid. MS: m/e=405.4 [M+H]+.

Workup

  1. customThe mixture was then evaporated
  2. custompurification by chromatography (silica, 0 to 100% ethyl acetate in heptane

Sources & evidence

ORD record
ord-55bb7da1e955481cb93876e0a50426a1
Source dataset
uspto-grants-2013_06
Patent number
US08466181B2

Reaction notes

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