HCID 89813173, compound → HCID 89813116, compound

HRID 1481198Notes

Reaction equation

HRID 1481198 reaction equation
C([O:5][C:6](=[O:34])[C:7]([CH3:33])([CH3:32])[CH2:8][NH:9][C:10]([C:12]1[N:13]=[C:14]([C:30]#[N:31])[C:15]2[C:20]([C:21]=1[OH:22])=[CH:19][CH:18]=[C:17]([O:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)[CH:16]=2)=[O:11])(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[C:30]([C:14]1[C:15]2[C:20](=[CH:19][CH:18]=[C:17]([O:23][CH:24]3[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]3)[CH:16]=2)[C:21]([OH:22])=[C:12]([C:10]([NH:9][CH2:8][C:7]([CH3:33])([CH3:32])[C:6]([OH:34])=[O:5])=[O:11])[N:13]=1)#[N:31]

Participants

3

Reactant 1

HCID 89813173HCID 89813173, compound

Product 1

HCID 89813116HCID 89813116, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A mixture of 3-[(1-cyano-7-cyclohexyloxy-4-hydroxy-isoquinoline-3-carbonyl)-amino]-2,2-dimethyl-propionic acid tert-butyl ester (55 mg, 0.118 mmol) in (½) TFA/CH2Cl2 (3 mL) was stirred at room temperature for 3 h and concentrated. Residue was taken up with 30 mL of water and the resultant suspension was basified by 1 N NaOH to pH=9-10. The clear solution was then acidified by 1 N HCl to pH=3-4. Precipitate was collected and dried. Crude product was triturated with MeOH (3 mL). Solid was collected and dried in vacuo to provide the title compound 8.6 mg (0.02 mmol) in 18% yield. LC-MS ESI−: 410.00 (M−1)−.

Workup

  1. concentrationconcentrated
  2. customPrecipitate was collected
  3. customdried
  4. customCrude product was triturated with MeOH (3 mL)
  5. customSolid was collected
  6. customdried in vacuo

Sources & evidence

ORD record
ord-709716ea93094090a50011c3a9c1421f
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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