Isopropylamine → HCID 59519179, compound

HRID 237386Notes

Reaction equation

HRID 237386 reaction equation
F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)[C:12]2N=CC=[CH:16][C:11]=2[N:10]=N1.[NH2:25][C:26]1[N:27]=[C:28]([C:38]2[CH:43]=[C:42]([O:44][CH2:45][C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[C:41]([Cl:52])=[CH:40][C:39]=2[Cl:53])[C:29]2[CH:34]=[C:33]([C:35]([OH:37])=O)[S:32][C:30]=2[N:31]=1.C(N)(C)C>CN(C=O)C>[CH:11]([NH:10][C:35]([C:33]1[S:32][C:30]2[N:31]=[C:26]([NH2:25])[N:27]=[C:28]([C:38]3[CH:43]=[C:42]([O:44][CH2:45][C:46]4[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=4)[C:41]([Cl:52])=[CH:40][C:39]=3[Cl:53])[C:29]=2[CH:34]=1)=[O:37])([CH3:16])[CH3:12]

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 44220506HCID 44220506, compound

Product 1

HCID 59519179HCID 59519179, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (1.176 g; 3.07 mmol) was added to 2-Amino-4-(5-benzyloxy-2,4-dichloro-phenyl)-thieno[2,3-d]pyrimidine-6-carboxylic acid. 2NaCl (1.33 g; 2.38 mmol) then DMF (25 ml) was added to afford a turbid brown solution. Isopropylamine (1.01 ml; 11.9 mmol) was added and reaction mixture was heated at 60° C. (oil bath temperature) for 18 hours. Reaction mixture was allowed to cool to room temperature and DMF was removed in vacuo. The residue was partitioned between ethyl acetate (200 ml) and water (200 ml). The phases were separated and the organic phase was washed with saturated aqueous sodium chloride solution (200 ml) the dried over anhydrous sodium sulphate, filtered and the filtrate solvents removed in vacuo to afford a yellow solid. The crude product was purified by flash chromatography on silica gel (50 g IST Flash Si cartridge) eluting with a solvent gradient of 20 to 50% ethyl acetate in hexane. This affords product as a colourless solid (0.612 g; 53%)

Workup

  1. customto afford a turbid brown solution
  2. customreaction mixture
  3. customReaction mixture
  4. temperatureto cool to room temperature
  5. customDMF was removed in vacuo
  6. customThe residue was partitioned between ethyl acetate (200 ml) and water (200 ml)
  7. customThe phases were separated
  8. washthe organic phase was washed with saturated aqueous sodium chloride solution (200 ml) the
  9. dry with materialdried over anhydrous sodium sulphate
  10. filtrationfiltered
  11. customthe filtrate solvents removed in vacuo
  12. customto afford a yellow solid
  13. customThe crude product was purified by flash chromatography on silica gel (50 g IST Flash Si cartridge)
  14. washeluting with a solvent gradient of 20 to 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-3bd16bf1edac42dabcd46e9faed0c10b
Source dataset
uspto-grants-2014_02
Patent number
US08642594B2

Reaction notes

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