Ethylamine hydrochloride → HCID 68813869, compound

HRID 2104989Notes

Reaction equation

HRID 2104989 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([O:58][CH:59]([CH3:61])[CH3:60])[C:7]([F:57])=[C:8]([CH:10]([NH:44][C:45]2[CH:50]=[CH:49][C:48]([C:51]3[N:55]=[C:54]([CH3:56])[O:53][N:52]=3)=[CH:47][CH:46]=2)[C:11]2[N:12]([C:25]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:13]=[C:14]([C:16]3[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=3[C:18](O)=[O:19])[N:15]=2)[CH:9]=1)[CH3:2].[NH2:62][CH2:63][CH3:64].Cl.C1C=NC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.C([O-])(O)=O.[Na+]>C(Cl)Cl.CN(C=O)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([O:58][CH:59]([CH3:61])[CH3:60])[C:7]([F:57])=[C:8]([CH:10]([NH:44][C:45]2[CH:50]=[CH:49][C:48]([C:51]3[N:55]=[C:54]([CH3:56])[O:53][N:52]=3)=[CH:47][CH:46]=2)[C:11]2[N:12]([C:25]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)([C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:13]=[C:14]([C:16]3[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=3[C:18]([NH:62][CH2:63][CH3:64])=[O:19])[N:15]=2)[CH:9]=1)[CH3:2]

Participants

7

Reactant 5

HCID 11198Ethylamine hydrochlorideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 516892Sodium BicarbonateHCID 68813792HCID 68813792, compound

Product 1

HCID 68813869HCID 68813869, compound

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

A mixture of Intermediate 133.1 (crude, ˜30 mg), NH2Et.HCl (7 mg, 0.13 mmol), HOAt (41 mg, 0.3 mmol), EDCI (58 mg, 0.3 mmol), NaHCO3 (50 mg, 0.6 mmol) in 4:1 CH2Cl2/DMF (2 mL) was stirred at rt for 2 h. The reaction mixture was then partitioned between EtOAc and sat. NaHCO3, the organic layer was then washed by NH4Cl, and sat. NaCl, the organic layer was collected and dried over (Na2SO4), filtered and concentrated to afford Intermediate 133.2. The crude material was used without further purification in the following step.

Workup

  1. customThe reaction mixture was then partitioned between EtOAc and sat. NaHCO3
  2. washthe organic layer was then washed by NH4Cl, and sat. NaCl
  3. customthe organic layer was collected
  4. dry with materialdried over (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-207eec6293a245be9b82325409ab471c
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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