Chloroform → HCID 86705472, compound

HRID 2279445Notes

Reaction equation

HRID 2279445 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:12][C:13]([N:15]2[CH2:24][CH2:23][C:22]3[CH:21]=[N:20][C:19]([NH:25][CH:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)=[N:18][C:17]=3[CH2:16]2)=[O:14])[C:9]([OH:11])=O)=[CH:4][C:3]=1[F:32].CCN=C=NCCCN(C)C.C(Cl)(Cl)Cl.[CH:48]([NH:50][NH2:51])=[O:49]>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:12][C:13]([N:15]2[CH2:24][CH2:23][C:22]3[CH:21]=[N:20][C:19]([NH:25][CH:26]4[CH2:27][CH2:28][O:29][CH2:30][CH2:31]4)=[N:18][C:17]=3[CH2:16]2)=[O:14])[C:9]([NH:51][NH:50][CH:48]=[O:49])=[O:11])=[CH:4][C:3]=1[F:32]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 12229HydrazinecarboxaldehydeHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 86705471HCID 86705471, compound

Product 1

HCID 86705472HCID 86705472, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 46 (270 mg, 0.582 mmol) and EDCI (139 mg, 0.728 mmol) and CHCl3 (10 mL) was added formohydrazide (41.9 mg, 0.698 mmol) and the reaction was stirred at RT for 2 h. Water was added and the mixture was extracted with DCM. The organic layer was separated and concentrated. The crude residue was purified by SiO2 chromatography eluting with a MeOH/DCM gradient (6 to 8% MeOH) to afford 119 mg (36.4%) of N-(1-(4-chloro-3-fluorophenyl)-2-(2-formylhydrazinyl)-2-oxoethyl)-2-(tetrahydro-2H-pyran-4-ylamino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxamide (48).

Workup

  1. extractionthe mixture was extracted with DCM
  2. customThe organic layer was separated
  3. concentrationconcentrated
  4. customThe crude residue was purified by SiO2 chromatography
  5. washeluting with a MeOH/DCM gradient (6 to 8% MeOH)

Sources & evidence

ORD record
ord-4c9755f36bd049f5ac2765e47823822e
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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