Morpholine → HCID 77107697, compound

HRID 63611Notes

Reaction equation

HRID 63611 reaction equation
[NH2:1][C:2]1[C:7]([Br:8])=[C:6]([NH:9][CH2:10][CH3:11])[N:5]=[C:4]([N:12]2[CH:16]=[C:15]([C:17]([OH:19])=O)[CH:14]=[N:13]2)[N:3]=1.[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(#N)C>[NH2:1][C:2]1[C:7]([Br:8])=[C:6]([NH:9][CH2:10][CH3:11])[N:5]=[C:4]([N:12]2[CH:16]=[C:15]([C:17]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[O:19])[CH:14]=[N:13]2)[N:3]=1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 771075031-[4-amino-5-bromo-6-(ethylamino)pyrimidin-2-yl]-1H-pyrazole-4-carboxylic acid

Product 1

HCID 77107697HCID 77107697, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 50 mg (0.15 mmol) of 1-[4-amino-5-bromo-6-(ethylamino)pyrimidin-2-yl]-1H-pyrazole-4-carboxylic acid (example 48), 15 μl (0.17 mmol) of morpholine, 32 μl (0.23 mmol) of triethylamine and 64 mg (0.17 mmol) of HATU in 1 ml of acetonitrile was stirred at room temperature for 10 min. The formed precipitate was filtered, washed with cold water and dried. 39 mg (64.4%) of a white solid were obtained.

Workup

  1. filtrationThe formed precipitate was filtered
  2. washwashed with cold water
  3. customdried

Sources & evidence

ORD record
ord-00ac308e671248cf857b52c9f82416a9
Source dataset
uspto-grants-2016_09
Patent number
US09447095B2

Reaction notes

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