Triethylamine → HCID 136384761, compound

HRID 494614Notes

Reaction equation

HRID 494614 reaction equation
Cl.[NH2:2][C:3]1[CH:32]=[CH:31][C:6]2[NH:7][C:8]([C:13]3[C:14](=[O:30])[C:15]([CH3:29])([CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])[C:16]4[C:21]([C:22]=3[OH:23])=[CH:20][CH:19]=[CH:18][CH:17]=4)=[N:9][S:10](=[O:12])(=[O:11])[C:5]=2[CH:4]=1.[C:33]([NH:37][S:38](Cl)(=[O:40])=[O:39])(=[O:36])[CH2:34][CH3:35].C(N(CC)CC)C>ClCCl>[OH:23][C:22]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH3:29])([CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])[C:14](=[O:30])[C:13]=1[C:8]1[NH:7][C:6]2[CH:31]=[CH:32][C:3]([NH:2][S:38]([NH:37][C:33](=[O:36])[CH2:34][CH3:35])(=[O:40])=[O:39])=[CH:4][C:5]=2[S:10](=[O:12])(=[O:11])[N:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 20138741HCID 20138741, compoundHCID 136375607HCID 136375607, compound

Product 1

HCID 136384761HCID 136384761, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of Example 34B (52.2 mg, 0.110 mmol) and the product of Example 100A (94.6 mg, 0.55 mmol) in dichloromethane (5 mL) was treated with triethylamine (66.5 mg, 0.658 mmol). The mixture was stirred at rt for 15 minutes. The reaction mixture was partitioned between dichloromethane and 1N hydrochloric acid, and the aqueous phase extracted with additional dichloromethane. The organic phase was dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by HPLC to give the title compound (36.3 mg, 57%). 1H NMR (300 MHz, DMSO-d6) δ 0.41 (s, 2H) 0.69 (d, J=6.62 Hz, 3H) 0.72 (d, J=6.62 Hz, 3H) 0.88 (t, J=7.54 Hz, 3H) 1.33 (m, 2H) 1.57 (s, 3H) 2.04 (m, 1H) 2.14 (q, J=7.35 Hz, 2H) 2.25 (m, J=13.97, 3.31 Hz, 1H) 7.48 (dd, J=9.01, 2.39 Hz, 1H) 7.54 (m, J=8.27, 3.86 Hz, 1H) 7.59 (d, J=2.21 Hz, 1H) 7.71 (d, J=8.82 Hz, 1H) 7.76 (d, J=3.68 Hz, 2H) 8.16 (d, J=8.09 Hz, 1H) 10.94 (s, 1H) 11.98 (s, 1H) 13.80 (s, 1H).). MS (ESI+) m/z 575.2 (M+H)+, 592.2 (M+NH4)+, (ESI−).

Workup

  1. customThe reaction mixture was partitioned between dichloromethane and 1N hydrochloric acid
  2. extractionthe aqueous phase extracted with additional dichloromethane
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-166ca56489014b54a0914739a7c631d9
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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