Ethylamine → HCID 49773783, compound

HRID 1025532Notes

Reaction equation

HRID 1025532 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]=[C:13]([NH:19][CH2:20][C:21]4[CH:26]=[CH:25][C:24]([S:27]([NH2:30])(=[O:29])=[O:28])=[CH:23][CH:22]=4)[N:14]=[C:15](O)[C:16]=3[N:17]=2)=[CH:4][CH:3]=1.C1C[N:34]([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)[CH2:33][CH2:32]1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.C(N)C>CN(C=O)C>[CH2:33]([NH:34][C:15]1[C:16]2[N:17]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[CH:9]=[CH:10][C:11]=2[N:12]=[C:13]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([S:27]([NH2:30])(=[O:29])=[O:28])=[CH:23][CH:22]=2)[N:14]=1)[CH3:32]

Participants

6

Reactant 4

HCID 6341EthylamineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 178514715HCID 178514715, compound

Product 1

HCID 49773783HCID 49773783, compoundYield 52.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-{[6-(4-Fluoro-phenyl)-4-hydroxy-pyrido[3,2-d]pyrimidin-2-ylamino]-methyl}-benzenesulfonamide (100 mg, 0.23 mmol) and PyBOP (119 mg, 0.23 mmol) were taken up in DMF (2 mL) and DIEA (0.07 mL, 0.46 mmol) was added, followed by ethylamine (2.0M in THF) (0.115 mL, 0.23 mmol) This solution was stirred at room temperature overnight. The DMF was removed in vacuo and the residue diluted with ethyl acetate (2 mL) and washed with water and brine. The organic layer was dried over sodium sulfate and concentrated to afford an oily residue. The residue was purified by RP HPLC using a C18 column with a 0-60% gradient of 0.1% TFA-H2O/0.1% TFA-acetonitrile to afford 55 mg (52%) of Example 297. MS (m/z) 453.4 [M+H]+.

Workup

  1. customThe DMF was removed in vacuo
  2. additionthe residue diluted with ethyl acetate (2 mL)
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated
  6. customto afford an oily residue
  7. customThe residue was purified by RP HPLC

Sources & evidence

ORD record
ord-8f0b95c09b91496fa38c88e3b073625e
Source dataset
uspto-grants-2014_05
Patent number
US08729089B2

Reaction notes

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