Diisopropylethylamine → HCID 67065479, compound

HRID 1967104Notes

Reaction equation

HRID 1967104 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[S:11][CH:10]=[C:9]([C:12]([OH:14])=O)[CH:8]=2)=[CH:5][CH:4]=[N:3]1.[NH2:15][CH:16]([C:29]([CH3:37])([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH3:30])[CH2:17][N:18]1[C:26](=[O:27])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]1=[O:28].C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>C(Cl)(Cl)Cl>[O:28]=[C:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:26](=[O:27])[N:18]1[CH2:17][CH:16]([NH:15][C:12]([C:9]1[CH:8]=[C:7]([C:6]2[N:2]([CH3:1])[N:3]=[CH:4][CH:5]=2)[S:11][CH:10]=1)=[O:14])[C:29]([CH3:30])([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH3:37]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 57826478HCID 57826478, compoundHCID 581103265-(1-methyl-1H-pyrazol-5-yl)-3-thiophenecarboxylic acid

Product 1

HCID 67065479HCID 67065479, compoundYield 29.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a heterogeneous mixture of 5-(1-methyl-1H-pyrazol-5-yl)-3-thiophenecarboxylic acid (155 mg, 0.74 mmol), 2-(2-amino-3-methyl-3-phenylbutyl)-1H-isoindole-1,3(2H)-dione (200 mg, 0.65 mmol)[from Preparation 4] and PyBrOP (426 mg, 0.91 mmol) in CHCl3 (10 mL) at 25° C. was added diisopropylethyl amine (0.5 mL, 2.9 mmol) dropwise. After 16 h, the mixture was adsorbed onto silica and the mixture purified via column chromatography (silica, 35-50% EtOAc/Hex) affording the title compound (96 mg, 26%) as a white solid: LC-MS (ES) m/z=499 (M+H)+.

Workup

  1. customthe mixture purified via column chromatography (silica, 35-50% EtOAc/Hex)

Sources & evidence

ORD record
ord-f199965ca73f4f3498708b9ce38470d2
Source dataset
uspto-grants-2013_04
Patent number
US08420690B2

Reaction notes

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