Isopropylamine → HCID 59568457, compound

HRID 1695503Notes

Reaction equation

HRID 1695503 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([OH:9])=O)=[CH:5][C:4]([NH:10][CH2:11][C:12]2[C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)=[N:14][O:15][C:16]=2[CH3:17])=[N:3]1.CN(C(O[N:32]1N=N[C:34]2C=CC=[CH:38][C:33]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)C(C)C)(C)C.C(N)(C)C>CN(C=O)C>[CH:33]([NH:32][C:7]([C:6]1[N:2]([CH3:1])[N:3]=[C:4]([NH:10][CH2:11][C:12]2[C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)=[N:14][O:15][C:16]=2[CH3:17])[CH:5]=1)=[O:9])([CH3:38])[CH3:34]

Participants

6

Reactant 4

HCID 6363IsopropylamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66646518HCID 66646518, compound

Product 1

HCID 59568457HCID 59568457, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-methyl-3-((5-methyl-3-(pyridin-2-yl)isoxazol-4-yl)methylamino)-1H-pyrazole-5-carboxylic acid (80 mg, 255 μmol) in DMF (3 mL) were added TBTU (91 mg, 281 μmol) and N,N-diisopropyl ethyl amine (217 μL, 1.28 mmol) followed by isopropylamine (24 μL, 281 μmol). The mixture was stirred at RT for 1 h, then evaporated. The residue was purified by flash-chromatography over NH2 silica gel using gradient EtOAc/heptane 10-70% to afford the title compound (75 mg, 83%) as a white solid. MS: m/e=355.2 [M+H]+.

Workup

  1. customevaporated
  2. customThe residue was purified by flash-chromatography over NH2 silica gel using gradient EtOAc/heptane 10-70%

Sources & evidence

ORD record
ord-7bcb4502e3a54ade933571d932e94429
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

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