1,2-Dichloroethane → HCID 57925952, compound

HRID 1013465Notes

Reaction equation

HRID 1013465 reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:7][O:6][P:5]([CH2:9][C:10]2[CH:18]=[CH:17][C:13]([C:14](O)=[O:15])=[CH:12][CH:11]=2)(=[O:8])[O:4][CH2:3]1.C(OC(=O)[NH:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[S:34][CH:35]=[CH:36][CH:37]=2)=[CH:29][C:28]=1[NH2:38])(C)(C)C.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C>[NH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[S:34][CH:35]=[CH:36][CH:37]=2)=[CH:29][C:28]=1[NH:38][C:14](=[O:15])[C:13]1[CH:17]=[CH:18][C:10]([CH2:9][P:5]2(=[O:8])[O:6][CH2:7][C:2]([CH3:19])([CH3:1])[CH2:3][O:4]2)=[CH:11][CH:12]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 57717474tert-Butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamateHCID 57925949HCID 57925949, compound

Product 1

HCID 57925952HCID 57925952, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(5,5-Dimethyl-2-oxo-2λ5-[1,3,2]dioxaphosphinan-2-ylmethyl)-benzoic acid (100 mg, 0.35 mmol), (2-amino-4-thiophen-2-yl-phenyl)-carbamic acid tert-butyl ester (123 mg, 0.42 mmol), EDC (81 mg, 0.42 mmol), HOBT (54 mg, 0.35 mmol), and DIPEA (136 mg, 1.05 mmol) were combined and diluted with DMF (1.4 mL). The resulting mixture was stirred at ambient temperature for 18 hours. The reaction mixture was purified directly by HPLC (20-85% MeCN in water w/0.025% TFA). Pure fractions were identified, combined and concentrated in vacuo. The residue was diluted with 10:1 DCM:TFA and stirred at ambient temperature for 2 hours. The mixture was then concentrated in vacuo to afford the title compound: 1H NMR (DMSO-d6, 600 MHz) δ 9.85 (s, 1H), 7.93 (d, J=7.2 Hz, 2H), 7.50 (s, 1H), 7.43 (d, J=7.2 Hz, 2H), 7.34-7.40 (m, 2H), 7.28-7.30 (m, 1H), 7.03-7.06 (m, 1H), 6.90-6.92 (m, 1H), 4.20-4.25 (m, 2H), 4.01 (br-s, 2H), 3.87-3.94 (m, 2H), 3.52 (d, J=20.4 Hz, 2H), 1.08 (s, 3H), 0.84 (s, 3H). MS: cal'd 457 (MH+), exp 457 (MH+).

Workup

  1. customThe reaction mixture was purified directly by HPLC (20-85% MeCN in water w/0.025% TFA)
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with 10:1 DCM
  4. stirringTFA and stirred at ambient temperature for 2 hours
  5. concentrationThe mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-267d9d5768794506ba213def5f9a5b61
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

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