1,2-Dichloroethane → HCID 57925952、化合物

HRID 1013465ノート

反応式

HRID 1013465 の反応式
[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

参加物

7

反応物 5

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

生成物 1

HCID 57925952HCID 57925952、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-267d9d5768794506ba213def5f9a5b61
出典データセット
uspto-grants-2011_07
特許番号
US07981874B2

反応ノート

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