Diisopropylethylamine → HCID 58413247, compound

HRID 532304Notes

Reaction equation

HRID 532304 reaction equation
C[N:2](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:25]([O:28][C:29]1[C:34]([NH:35][C:36]2[C:37]3[C:44]([CH3:45])=[C:43]([C:46]([OH:48])=O)[S:42][C:38]=3[N:39]=[CH:40][N:41]=2)=[CH:33][CH:32]=[CH:31][N:30]=1)([CH3:27])[CH3:26].CCN(C(C)C)C(C)C.N.CO>CN(C=O)C.CCOC(C)=O>[CH:25]([O:28][C:29]1[C:34]([NH:35][C:36]2[C:37]3[C:44]([CH3:45])=[C:43]([C:46]([NH2:2])=[O:48])[S:42][C:38]=3[N:39]=[CH:40][N:41]=2)=[CH:33][CH:32]=[CH:31][N:30]=1)([CH3:26])[CH3:27]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 21705897Ammonia methanolHCID 46182084HCID 46182084, compound

Product 1

HCID 58413247HCID 58413247, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

HATU (182.0 mg) was added to an ice cooled solution of 150 mg 4-(2-Isopropoxypyridin-3-ylamino)-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid and DIPEA (83.0 μl) in DMF (3.0 ml). The mixture was stirred at 0° C. for 20 min then ammonia/MeOH (7M; 1.5 ml) was added and it was allowed to warm to room temperature overnight. The mixture was diluted with EtOAc and washed with water, 2M NaOH and concentrated in vacuo. The residue was triturated with Et2O and filtered to give the title compound.

Workup

  1. temperatureto warm to room temperature overnight
  2. washwashed with water, 2M NaOH
  3. concentrationconcentrated in vacuo
  4. customThe residue was triturated with Et2O
  5. filtrationfiltered

Sources & evidence

ORD record
ord-671b82b60ff343478a1df6fcbb4a7e4d
Source dataset
uspto-grants-2014_10
Patent number
US08853193B2

Reaction notes

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