Isopropylamine → HCID 57329859, compound

HRID 2365240Notes

Reaction equation

HRID 2365240 reaction equation
[CH3:1][C:2]1[N:3]=[C:4](/[CH:10]=[CH:11]/[C:12]2[N:13]([CH3:23])[N:14]=[N:15][C:16]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[S:5][C:6]=1[C:7]([OH:9])=O.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.CCN(C(C)C)C(C)C.C(N)(C)C>CN(C=O)C>[CH:33]([NH:32][C:7]([C:6]1[S:5][C:4](/[CH:10]=[CH:11]/[C:12]2[N:13]([CH3:23])[N:14]=[N:15][C:16]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)=[N:3][C:2]=1[CH3:1])=[O:9])([CH3:38])[CH3:34]

Participants

6

Reactant 4

HCID 6363IsopropylamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67496730HCID 67496730, compound

Product 1

HCID 57329859HCID 57329859, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-methyl-2-[(E)-2-(3-methyl-5-pyridin-2-yl-3H-[1,2,3]triazol-4-yl)-vinyl]-thiazole-5-carboxylic acid (56 mg, 0.17 mmol) and TBTU (60 mg, 0.19 mmol) in DMF (0.9 mL) was added DIPEA (146 μL, 0.86 mmol). Then isopropylamine (16 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 10% methanol in dichloromethane) afforded the title compound (36 mg, 57%) as a light yellow solid after recrystallisation from methanol-water. MS: m/e=369.2 [M+H]+.

Workup

  1. customThe mixture was then evaporated
  2. custompurification by chromatography (silica, 1 to 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-991cf631ab694b59aa7a81a4d3153f2f
Source dataset
uspto-grants-2014_04
Patent number
US08697696B2

Reaction notes

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