Ammonia → HCID 24993043, compound

HRID 2090220Notes

Reaction equation

HRID 2090220 reaction equation
[CH2:1]([O:3][C:4]1[N:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]([C:22]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][C:23]=1[O:30][CH3:31])[C:7]([C:15]([N:17]1C=CN=C1)=[O:16])=[C:8]([CH3:14])[NH:9]2)[CH3:2].N>CN(C=O)C>[C:26]([C:25]1[CH:28]=[CH:29][C:22]([CH:6]2[C:5]3[C:10](=[CH:11][CH:12]=[N:13][C:4]=3[O:3][CH2:1][CH3:2])[NH:9][C:8]([CH3:14])=[C:7]2[C:15]([NH2:17])=[O:16])=[C:23]([O:30][CH3:31])[CH:24]=1)#[N:27]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 59349648HCID 59349648, compound

Product 1

HCID 24993043HCID 24993043, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

100 mg (approx. 0.24 mmol) of the compound from Example 23A are introduced into 3 ml of DMF. Then 2.94 mg (0.024 mmol) of 4-N,N-dimethylaminopyridine and 340 μl of ammonia (28% by weight solution in water, 2.41 mmol) are added, and the mixture is heated at 100° C. for 3 h. After cooling, the crude product is directly purified by preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid, gradient 20:80→95:5). 32 mg (37% of theory) of the title compound are obtained.

Workup

  1. temperatureAfter cooling
  2. customthe crude product is directly purified by preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid, gradient 20:80→95:5)

Sources & evidence

ORD record
ord-260de2b76b3141c4a4c09b41824f2e9c
Source dataset
uspto-grants-2013_05
Patent number
US08436180B2

Reaction notes

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