Dichloromethane → HCID 178479220, compound

HRID 717745Notes

Reaction equation

HRID 717745 reaction equation
C(OC(=O)[N:7]([CH2:29][CH2:30][CH2:31][NH:32]C(OC(C)(C)C)=O)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16](=[O:28])[N:17]=[C:18]3[NH:23][C:22]4[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=4[N:19]3[CH:20]=2)=[CH:11][CH:10]=1)(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)[Cl:49]>>[ClH:49].[NH2:32][CH2:31][CH2:30][CH2:29][NH:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[C:16](=[O:28])[N:17]=[C:18]3[NH:23][C:22]4[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=4[N:19]3[CH:20]=2)=[CH:13][CH:14]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 178453511HCID 178453511, compound

Product 1

HCID 178479220HCID 178479220, compoundYield 100%

Procedure

Compound 5 (170 mg, 0.31 mmol) was dissolved in CH2Cl2 (5 mL), TFA (1 mL) was added and stirred at room temperature for 2 h. The reaction mixture was concentrated and 3 mL of 0.6 N HCl and 2 mL of acetonitrile were added and stirred for 0.5 h, concentrated to a ca. 3 mL and lyophilized to give the title compound (150 mg, 100%). 1NMR (300 MHz, CD3OD): δ 9.43 (s, 1H), 8.27 (d, J=8.2 Hz, 1H), 7.87 (d, J=7.8 Hz, 2H), 7.75 (d, J=7.8 Hz, 3H), 7.69 (t, J=8.2 Hz, 1H), 7.62 (t, J=8.2 Hz, 1H), 4.35 (s, 2H), 3.25 (t, J=8.1 Hz, 2H), 3.10 (t, J=7.5 Hz, 2H), 2.18 (m, 2H). LCMS (EI) m/z: 348.1 (M+H+).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. addition3 mL of 0.6 N HCl and 2 mL of acetonitrile were added
  3. stirringstirred for 0.5 h
  4. concentrationconcentrated to a ca. 3 mL

Sources & evidence

ORD record
ord-b3cb7a3d517a44fbb1e78ee74a16e63e
Source dataset
uspto-grants-2015_11
Patent number
US09193731B2

Reaction notes

Loading…