Ammonia → HCID 10074074, compound

HRID 747113Notes

Reaction equation

HRID 747113 reaction equation
[CH2:1]([N:3]([CH2:35][CH3:36])[C:4]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]([N:22]2[CH2:27][CH2:26][N:25]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:24][CH2:23]2)[C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=2)[C:16]([OH:18])=O)=[CH:8][CH:7]=1)=[O:5])[CH3:2].ClC(OCC(C)C)=O.C([N:47](CC)CC)C.N>ClCCl>[CH2:35]([N:3]([CH2:1][CH3:2])[C:4]([C:6]1[CH:7]=[CH:8][C:9]([CH:12]([N:22]2[CH2:27][CH2:26][N:25]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:24][CH2:23]2)[C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=2)[C:16]([NH2:47])=[O:18])=[CH:10][CH:11]=1)=[O:5])[CH3:36]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 58677817HCID 58677817, compound

Product 1

HCID 10074074HCID 10074074, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of INTERMEDIATE 9 (100 mg, 0.21 mmol) in dichloromethane (3 mL) at −20° C. was added isobutyl chloroformate (41 μL, 0.31 mmol) and triethylamine (43 μL, 0.31 mmol). After 10 minutes a solution of ammonia in dichloromethane (1.5M, 4.5 mL, 3 mmol) was added. Reacton was warmed to room temperature and washed with brine. The organic layer was dried (MgSO4), filtered and concentrated to give COMPOUND 1.

Workup

  1. washwashed with brine
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d95cdc20f01145a588c6f0c7cc97148d
Source dataset
uspto-grants-2008_07
Patent number
US07396834B2

Reaction notes

Loading…