Methyl chloroformate → HCID 178501937, compound

HRID 2114637Notes

Reaction equation

HRID 2114637 reaction equation
[Cl:1][C:2]([O:4][CH3:5])=[O:3].[Cl:6][C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([O:15][C:16]2[C:17]([CH3:28])=[N:18][NH:19][C:20]=2[CH2:21][N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH:14]=1)[C:10]#[N:11].C(N(CC)CC)C>ClCCl>[Cl:6][CH2:2][Cl:1].[CH3:13][OH:15].[NH3:11].[Cl:6][C:7]1[CH:14]=[C:13]([CH:12]=[C:9]([C:10]#[N:11])[CH:8]=1)[O:15][C:16]1[C:17]([CH3:28])=[N:18][NH:19][C:20]=1[CH2:21][N:22]1[CH2:27][CH2:26][N:25]([C:2]([O:4][CH3:5])=[O:3])[CH2:24][CH2:23]1

Participants

6

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 178434619HCID 178434619, compound

Product 2

HCID 21584172Ammonia methanol dichloromethaneHCID 178501937HCID 178501937, compoundYield 117.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl chloroformate (19 μl, 0.240 mmol) was added dropwise to a stirred solution of the amine of Example 78 (80 mg, 0.240 mmol) and triethylamine (45 μl, 0.288 mmol) in dichloromethane (5 ml) at room temperature under nitrogen. The reaction was stirred for 90 minutes and then concentrated under reduced pressure to leave a yellow oil. The crude product was purified by flash column chromatography on silica gel eluting with dichloromethane and then dichloromethane:methanol:ammonia (95:4:1, by volume) to provide the title compound (55 mg) as a white foam.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto leave a yellow oil
  3. customThe crude product was purified by flash column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-2b7534fed4494978b539dcef58906c20
Source dataset
uspto-grants-2008_10
Patent number
US07435728B2

Reaction notes

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