Hydrochloric Acid → HCID 59536789, compound

HRID 2402847Notes

Reaction equation

HRID 2402847 reaction equation
[CH2:1]([NH:3][C:4](=[O:42])[O:5][CH2:6][CH:7]([NH:18][C:19](=[O:41])[CH2:20][N:21]1[C:25](=[O:26])[N:24]([CH2:27][C@H:28](O)[C:29]([F:32])([F:31])[F:30])[C:23]([C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=2)=[N:22]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]([F:17])([F:16])[F:15])[CH3:2].Cl>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[CH2:1]([NH:3][C:4](=[O:42])[O:5][CH2:6][CH:7]([NH:18][C:19](=[O:41])[CH2:20][N:21]1[C:25](=[O:26])[N:24](/[CH:27]=[CH:28]/[C:29]([F:32])([F:31])[F:30])[C:23]([C:34]2[CH:35]=[CH:36][C:37]([Cl:40])=[CH:38][CH:39]=2)=[N:22]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]([F:17])([F:16])[F:15])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59536936HCID 59536936, compound

Product 1

HCID 59536789HCID 59536789, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A solution of 230 mg (0.37 mmol) of the compound from Example 145 and 54 mg (0.44 mmol) of DMAP in 5 ml of pyridine was admixed dropwise with 155 μl (0.92 mmol) of trifluoromethanoic anhydride and the resulting mixture was stirred at RT overnight. Subsequently 2 ml of 1N hydrochloric acid were added and the volatile components were removed on a rotary evaporator. The residue was dissolved in a little DMSO and purified by preparative HPLC [Method 10]. The product-containing fraction was freed from the solvents on a rotary evaporator and the residue was dried in an HV. This gave 168 mg (75% of theory) of the title compound.

Workup

  1. customthe volatile components were removed on a rotary evaporator
  2. dissolutionThe residue was dissolved in a little DMSO
  3. custompurified by preparative HPLC [Method 10]
  4. customThe product-containing fraction was freed from the solvents on a rotary evaporator
  5. customthe residue was dried in an HV

Sources & evidence

ORD record
ord-5c06598eb9964f1a96d3aa40b6e2cce8
Source dataset
uspto-grants-2014_08
Patent number
US08796324B2

Reaction notes

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