Triethylamine → HCID 136375606, compound

HRID 494612Notes

Reaction equation

HRID 494612 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:38][S:39](Cl)(=[O:41])=[O:40])(=[O:37])[CH2:34][CH2:35][CH3:36].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:39]([NH:38][C:33](=[O:37])[CH2:34][CH2:35][CH3:36])(=[O:41])=[O:40])=[CH:4][C:5]=2[S:10](=[O:12])(=[O:11])[N:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 45119351HCID 45119351, compoundHCID 136375607HCID 136375607, compound

Product 1

HCID 136375606HCID 136375606, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of the product of Example 34B (52.2 mg, 0.110 mmol) and the product of Example 99A (102 mg, 0.55 mmol) in dichloromethane (5 mL) was treated with triethylamine (66.5 mg, 0.658 mmol). The mixture was stirred at r.t. 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 (38 mg, 59%). 1H NMR (300 MHz, DMSO-d6) δ 0.41 (m, 1H) 0.69 (m, 9H) 0.79 (m, 1H) 1.37 (m, 4H) 1.56 (s, 3H) 2.04 (m, 1H) 2.11 (t, J=7.35 Hz, 2H) 2.22 (m, 1H) 7.48 (dd, J=8.82, 2.21 Hz, 1H) 7.53 (m, 1H) 7.59 (d, J=2.21 Hz, 1H) 7.71 (d, J=8.82 Hz, 1H) 7.76 (d, J=4.04 Hz, 2H) 8.15 (d, J=7.72 Hz, 1H) 10.95 (s, 1H) 11.99 (s, 1H) 13.81 (s, 1H). MS (ESI+) m/z 589.1 (M+H)+, 606.1 (M+NH4)+, (ESI−) 587.2 (M−H).

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-6e44d68fcfbc459d84da75b05a0891b8
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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