Diisopropylethylamine → HCID 57925828, compound

HRID 1013496Notes

Reaction equation

HRID 1013496 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)=[CH:10][C:9]=1[NH:19][C:20](=[O:29])[C:21]1[CH:26]=[CH:25][C:24]([CH2:27]Br)=[CH:23][CH:22]=1)(C)(C)C.Cl.[CH3:32][P:33]1(=[O:44])[O:38][CH2:37][C:36]2([CH2:43][CH2:42][NH:41][CH2:40][CH2:39]2)[CH2:35][O:34]1.CCN(C(C)C)C(C)C>CN(C=O)C.C([O-])(O)=O.[Na+]>[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)=[CH:10][C:9]=1[NH:19][C:20](=[O:29])[C:21]1[CH:22]=[CH:23][C:24]([CH2:27][N:41]2[CH2:42][CH2:43][C:36]3([CH2:35][O:34][P:33]([CH3:32])(=[O:44])[O:38][CH2:37]3)[CH2:39][CH2:40]2)=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 57925962Tert-butyl [2-{[4-(bromomethyl)benzoyl]amino}-4-(2-thienyl)phenyl]carbamateHCID 86635273HCID 86635273, compound

Product 1

HCID 57925828HCID 57925828, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

[2-(4-Bromomethyl-benzoylamino)-4-thiophen-2-yl-phenyl]-carbamic acid tert-butyl ester (150 mg, 0.31 mmol), 3-methyl-2,4-dioxa-9-aza-3-phosphaspiro[5.5]undecane 3-oxide hydrochloride (89 mg, 0.37 mmol), and DIEA (107 μL, 0.62 mmol) were combined in DMF (4 mL) and stirred at room temperature for 18 h. The solution was diluted with saturated NaHCO3 and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried (MgSO4), and evaporated. Flash chromatography of the crude (0-10% MeOH/CH2Cl2) afforded the desired product as a colorless solid. The solid was dissolved in a mixture of CH2Cl2 (4 mL) and TFA (1 mL) and stirred at room temperature for 2 h. The solution was diluted with 1,2-DCE and evaporated. The crude was taken up in EtOAc, washed with saturated NaHCO3 and brine, dried (MgSO4), and evaporated. The residue was triturated with EtOAc and filtered to afford the desired product as a colorless solid 1H NMR (DMSO-d6, 600 MHz) δ 9.69 (s, 1H), 7.94 (d, J=7.6 Hz, 2H), 7.44 (s, 1H), 7.41 (d, J=7.8 Hz, 2H), 7.33 (d, J=5.2 Hz, 1H), 7.27 (d, J=8.0 Hz, 1H), 7.22 (d, J=3.5 Hz, 1H), 7.02 (t, J=4.2 Hz, 1H), 6.79 (d, J=8.2 Hz, 1H), 5.13 (s, 2H), 4.16-4.04 (m, 4H), 3.54 (s, 2H), 2.43-2.37 (m, 2H), 2.34-2.28 (m, 2H), 1.68-1.62 (m, 2H), 1.52 (d, J=17.0 Hz, 3H), 1.42-1.38 (m, 2H). MS: cal'd 512 (MH+), exp 512 (MH+).

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-6356095f5ad540f9b674b39c5d328f3a
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

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