Acetonitrile → HCID 118159538, compound

HRID 628271Notes

Reaction equation

HRID 628271 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:8][C:9]1[N:13]2[C:14]3[CH:20]=[C:19]([CH3:21])[N:18]([CH2:22][C:23]4[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=4)[C:26](N)=[O:27])[C:15]=3[CH:16]=[CH:17][C:12]2=[N:11][N:10]=1.Cl.[NH2:33][OH:34].C(N(C(C)C)CC)(C)C.CC#N>C(Cl)Cl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:8][C:9]1[N:13]2[C:14]3[CH:20]=[C:19]([CH3:21])[N:18]([CH2:22][C:23]4[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=4)[C:26]([NH:33][OH:34])=[O:27])[C:15]=3[CH:16]=[CH:17][C:12]2=[N:11][N:10]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 118159795HCID 118159795, compound

Product 1

HCID 118159538HCID 118159538, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

One-third portion of the crude acid chloride (0.077 mmol) from Example 30, Step 2 was added to a solution of hydroxylamine HCl (0.048 g, 0.69 mmol, Aldrich) and diisopropylethylamine (0.12 mL, 0.69 mmol) in DCM (1 mL). MeCN (1 mL) was added and the reaction was stirred overnight. DCM was removed in vacuo and the reaction mixture was diluted with MeOH, filtered and purified by preparative HPLC-MS (Waters SunFire C18, eluting with a gradient of MeCN/H2O containing 0.1% TFA) (10 mg, 29%).

Workup

  1. customDCM was removed in vacuo
  2. additionthe reaction mixture was diluted with MeOH
  3. filtrationfiltered
  4. custompurified by preparative HPLC-MS (Waters SunFire C18
  5. washeluting with a gradient of MeCN/H2O containing 0.1% TFA) (10 mg, 29%)

Sources & evidence

ORD record
ord-11865e0743304453ac0ac91704030678
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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