HCID 59568585, compound → HCID 49783984, compound

HRID 216972Notes

Reaction equation

HRID 216972 reaction equation
[C:1]([C@@H:3]([NH:27][C:28]([C:30]1([NH:36]C(=O)OC(C)(C)C)[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1)=[O:29])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([N:20]3[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]3)(=[O:19])=[O:18])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)#[N:2]>C(O)=O>[NH2:36][C:30]1([C:28]([NH:27][C@H:3]([C:1]#[N:2])[CH2:4][C:5]2[CH:6]=[CH:7][C:8]([C:11]3[CH:12]=[CH:13][C:14]([S:17]([N:20]4[CH2:21][CH2:22][N:23]([CH3:26])[CH2:24][CH2:25]4)(=[O:18])=[O:19])=[CH:15][CH:16]=3)=[CH:9][CH:10]=2)=[O:29])[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1

Participants

3

Reactant 1

HCID 59568585HCID 59568585, compound

Product 1

HCID 49783984HCID 49783984, compoundYield 20.6%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

(S)-tert-Butyl 4-(1-cyano-2-(4′-(4-methylpiperazin-1-ylsulfonyl)biphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 29, step (ii), 250 mg) in formic acid (2 mL) was heated at 50° C. for 20 min. Volatiles were removed under reduced pressure and then azeotroped with methanol. The product was purified by reversed phase HPLC using methanol in 0.1% aqueous TFA as eluent. The residue was converted to the free base by elution through a PL-HCO3 MP cartridge in dichloromethane/methanol to afford the titled compound (43 mg).

Workup

  1. customVolatiles were removed under reduced pressure
  2. customazeotroped with methanol
  3. customThe product was purified by reversed phase
  4. washThe residue was converted to the free base by elution through a PL-HCO3 MP cartridge in dichloromethane/methanol

Sources & evidence

ORD record
ord-2958ae81ec7340fa9ac4497958f20ba2
Source dataset
uspto-grants-2012_06
Patent number
US08193239B2

Reaction notes

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