Dichloromethane → HCID 10928593, compound

HRID 2167065Notes

Reaction equation

HRID 2167065 reaction equation
[CH:1]1([CH2:4][NH:5][CH2:6][CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][NH:18][C:19]3[C:28]4[C:23](=[CH:24][C:25]([Cl:29])=[CH:26][CH:27]=4)[N:22]=[CH:21][CH:20]=3)[CH2:11][CH2:10]2)[CH2:3][CH2:2]1.[CH2:30](Cl)Cl.C(N([CH2:38][CH3:39])CC)C.[BH4-].[Na+]>O>[CH:1]1([CH2:4][NH:5][CH2:6][CH2:7][CH2:8][N:9]2[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][CH2:17][NH:18][C:19]3[C:28]4[C:23](=[CH:24][C:25]([Cl:29])=[CH:26][CH:27]=4)[N:22]=[CH:21][CH:20]=3)[CH2:13][CH2:14]2)[CH2:3][CH2:2][CH2:39][CH2:38][CH2:30]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 10905789HCID 10905789, compound2×

Product 1

HCID 10928593HCID 10928593, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of N4-3-[4(3-aminopropyl)piperazine]propyl-7-chloroquinolin-4-amine (Intermediate of example 12) (150 mg, 0.41 mmol) in CH2Cl2 (4 mL) cyclohexane-1-carboxaldehyde (83 μL, 0.46 mmol), triethylamine (26 μL, 0.16 mmol) and 3 Å molecular sieves are added. The reaction media is stirred for 3 h and cooled before NaBH4 (78 mg, 2.05 mmol) is added portionwise over 30 min. Stirring is left for 1.5 h, water (10 mL) is added and the media is filtered. Compound is extracted with CH2Cl2 (3×20 mL). Combined organic layers are dried over MgSO4. Crude compound is purified by thick-layer chromatography (CH2Cl2/MeOH/NH4OH:90/10/1.4).

Workup

  1. customThe reaction media
  2. additionis added portionwise over 30 min
  3. stirringStirring
  4. waitis left for 1.5 h
  5. filtrationthe media is filtered
  6. extractionCompound is extracted with CH2Cl2 (3×20 mL)
  7. dry with materialCombined organic layers are dried over MgSO4
  8. customCrude compound is purified by thick-layer chromatography (CH2Cl2/MeOH/NH4OH:90/10/1.4)

Sources & evidence

ORD record
ord-f45df0cd556343bb9447db17e62f0726
Source dataset
uspto-grants-2015_06
Patent number
US09044478B2

Reaction notes

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