1,2-Dichloroethane → HCID 117844257, compound

HRID 1481076Notes

Reaction equation

HRID 1481076 reaction equation
[C:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:11]=2)[C:6]([OH:20])=[C:5]([C:21](O)=[O:22])[N:4]=1)#[N:2].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[C:38]([O:42][C:43](=[O:49])[C@H:44]([CH3:48])[C@@H:45]([NH2:47])[CH3:46])([CH3:41])([CH3:40])[CH3:39].CCN(C(C)C)C(C)C.Cl>C(Cl)Cl>[C:38]([O:42][C:43](=[O:49])[C@H:44]([CH3:48])[C@@H:45]([NH:47][C:21]([C:5]1[N:4]=[C:3]([C:1]#[N:2])[C:12]2[C:7]([C:6]=1[OH:20])=[CH:8][CH:9]=[C:10]([O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:11]=2)=[O:22])[CH3:46])([CH3:39])([CH3:41])[CH3:40]

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 13979009HCID 13979009, compoundHCID 89812857HCID 89812857, compound

Product 1

HCID 117844257HCID 117844257, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A flask was charged with 1-cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid (40 mg, 0.13 mmol), HOBt (18 mg, 0.13 mmol) and CH2Cl2 (2 mL). EDC (35 mg, 0.18 mmol) was added, and the mixture was stirred for 10 min. (2R,3S)-3-Amino-2-methyl-butyric acid tert-butyl ester (22 mg, 0.13 mmol) and Hunig's base (0.050 mL, 0.26 mmol) were then added, and the resulting mixture was stirred for 3 days at r.t. Hydrochloric acid (0.1 M) was added to acidify the mixture, and the mixture was extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated. The crude product was purified by column chromatography (0-10% EtOAc/hexanes+2% AcOH) to give 30 mg of the title compound as a white solid. MS: (−) m/z 460.31 (M−1).

Workup

  1. additionwere then added
  2. extractionthe mixture was extracted with EtOAc
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography (0-10% EtOAc/hexanes+2% AcOH)

Sources & evidence

ORD record
ord-47ec8c095db5483d879b22417fd1adc5
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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