Methyl chloroformate → HCID 178501937, compound

HRID 558273Notes

Reaction equation

HRID 558273 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-21565cff88f44da0877261d543186715
Source dataset
uspto-grants-2011_11
Patent number
US08063044B2

Reaction notes

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