Diisopropylethylamine → 1,1-dimethylethyl [2-({[5-(1-methyl-1H-pyrazol-5-yl)-3-thienyl]carbonyl}amino)-2-(1-naphthalenyl)ethyl]carbamate

HRID 1967110Notes

Reaction equation

HRID 1967110 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.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[NH2:48][CH:49]([C:59]1[C:68]2[C:63](=[CH:64][CH:65]=[CH:66][CH:67]=2)[CH:62]=[CH:61][CH:60]=1)[CH2:50][NH:51][C:52](=[O:58])[O:53][C:54]([CH3:57])([CH3:56])[CH3:55]>C(Cl)Cl>[CH3:1][N:2]1[C:6]([C:7]2[S:11][CH:10]=[C:9]([C:12]([NH:48][CH:49]([C:59]3[C:68]4[C:63](=[CH:64][CH:65]=[CH:66][CH:67]=4)[CH:62]=[CH:61][CH:60]=3)[CH2:50][NH:51][C:52](=[O:58])[O:53][C:54]([CH3:57])([CH3:55])[CH3:56])=[O:14])[CH:8]=2)=[CH:5][CH:4]=[N:3]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 578264871,1-Dimethylethyl [2-amino-2-(1-naphthalenyl)ethyl]carbamateHCID 581103265-(1-methyl-1H-pyrazol-5-yl)-3-thiophenecarboxylic acid

Product 1

HCID 581729281,1-dimethylethyl [2-({[5-(1-methyl-1H-pyrazol-5-yl)-3-thienyl]carbonyl}amino)-2-(1-naphthalenyl)ethyl]carbamateYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(1-methyl-1H-pyrazol-5-yl)-3-thiophenecarboxylic acid (104 mg, 0.5 mmol), PyBrOP (384 mg, 0.83 mmol) and diisopropylethyl amine (0.14 mL, 0.83 mmol) in DCM (8 mL) at 25° C. was added 1,1-dimethylethyl [2-amino-2-(1-naphthalenyl)ethyl]carbamate (144 mg, 0.5 mmol) [from Preparation 6]. After 16 h, the solution was partitioned between H2O and washed with DCM. The combined organic fractions were dried (Na2SO4), concentrated and purified via column chromatography (silica) affording the title compound (76 mg, 32%) as a white solid: LC-MS (ES) m/z=477 (M+H)+.

Workup

  1. customthe solution was partitioned between H2O
  2. washwashed with DCM
  3. dry with materialThe combined organic fractions were dried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified via column chromatography (silica)

Sources & evidence

ORD record
ord-51c0538943204da69b757795ea1eacdc
Source dataset
uspto-grants-2013_04
Patent number
US08420690B2

Reaction notes

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