Dichloromethane → Hydrochloric Acid

HRID 2416217Notes

Reaction equation

HRID 2416217 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[S:8][CH:9]=[C:10]([C:12]3[C:13](=[O:24])[NH:14][C:15]4[C:20]([CH:21]=3)=[CH:19][CH:18]=[C:17]([CH:22]=[O:23])[CH:16]=4)[N:11]=2)=[CH:3][CH:2]=1.C(OC)(OC)OC.CC1CCCNC1.[OH-].[NH4+].C(Cl)[Cl:42]>CN(C=O)C.CCN(CC)CC.CC(O)=O>[ClH:42].[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[S:8][CH:9]=[C:10]([C:12]3[C:13](=[O:24])[NH:14][C:15]4[C:20]([CH:21]=3)=[CH:19][CH:18]=[C:17]([CH:22]=[O:23])[CH:16]=4)[N:11]=2)=[CH:3][CH:2]=1

Participants

10

Reactant 5

HCID 6344DichloromethaneHCID 9005Trimethyl orthoformateHCID 14923Ammonium HydroxideHCID 790813-MethylpiperidineHCID 22638533HCID 22638533, compound

Product 2

HCID 313Hydrochloric AcidHCID 22638533HCID 22638533, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 3-(2-pyridin-4-yl-thiazol-4-yl)-1H-quinolin-2-one-7-carbaldehyde (step (a), 60 mg, 0.18 mmol), 1 mL of CH2Cl2, 0.5 mL of trimethyl orthoformate, 3-methylpiperidine (0.2 mL), and 10 mL of 5% HOAc in DMF was allowed to stir for 2 h. At this time, 0.9 g of polymer bounded MP-NEt3:BH3(CN) (Argonaut, 1 mmol/g) was added and the mixture was stirred at RT overnight. The resins were carefully removed by filtration and the filtrate was concentrated. The resulting residue was dissolved in DMSO and purified by preparative HPLC. The solid obtained after lyophilization was neutralized with aqueous ammonium hydroxide and subsequently lyophilized. Treatment with excess 1 N HCl solution afforded the title compound as a yellow solid after lyophilization (HCl salt). MS m/z: 417.0 (M+1).

Workup

  1. additionBH3(CN) (Argonaut, 1 mmol/g) was added
  2. stirringthe mixture was stirred at RT overnight
  3. customThe resins were carefully removed by filtration
  4. concentrationthe filtrate was concentrated
  5. dissolutionThe resulting residue was dissolved in DMSO
  6. custompurified by preparative HPLC
  7. customThe solid obtained after lyophilization

Sources & evidence

ORD record
ord-f83c5a74097341d29da6c39a455b2e60
Source dataset
uspto-grants-2004_11
Patent number
US06822097B1

Reaction notes

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