Hydrochloric Acid → HCID 178474972, compound

HRID 887828Notes

Reaction equation

HRID 887828 reaction equation
Cl.Cl.[NH2:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([CH2:10][CH2:11][N:12]2[CH2:16][C@H:15]3[C:17]4[CH:18]=[C:19]([C:25]#[N:26])[CH:20]=[CH:21][C:22]=4[O:23][CH2:24][C@@H:14]3[CH2:13]2)[CH2:6][CH2:5]1.C(N(CC)CC)C.[C:34]([Cl:37])(=[O:36])[CH3:35].Cl>ClCCl.C(O)C>[ClH:37].[C:25]([C:19]1[CH:20]=[CH:21][C:22]2[O:23][CH2:24][C@H:14]3[C@H:15]([C:17]=2[CH:18]=1)[CH2:16][N:12]([CH2:11][CH2:10][C@H:7]1[CH2:8][CH2:9][C@H:4]([NH:3][C:34](=[O:36])[CH3:35])[CH2:5][CH2:6]1)[CH2:13]3)#[N:26]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 178478680HCID 178478680, compound

Product 1

HCID 178474972HCID 178474972, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 699 mg (2.1 mmol) of the compound of Example 1 in 15 ml of dichloromethane there are added, at ambient temperature, 354 μl of triethylamine (1.2 eq.) and then 164 μl of acetyl chloride (1.1 eq.). After stirring for 2 hours at ambient temperature, the mixture is washed with water and dried (MgSO4). Evaporating off the solvent followed by purifying on a silica column using a mixture of dichloromethane/methanol/ammonium hydroxide (97/3/0.3) as eluant yields, after converting to a salt in ethanol in the warm state using 1N ethereal HCl, the title product in the form of a white powder.

Workup

  1. washthe mixture is washed with water
  2. dry with materialdried (MgSO4)
  3. customEvaporating off the solvent
  4. customby purifying on a silica column
  5. additiona mixture of dichloromethane/methanol/ammonium hydroxide (97/3/0.3) as eluant
  6. customyields

Sources & evidence

ORD record
ord-b197723fefdf4988926e09193f855aa5
Source dataset
uspto-grants-2012_08
Patent number
US08247441B2

Reaction notes

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