Dichloromethane → (1h-Benzimidazol-2-yl)-{3-[4-(3-isobutylamino-propyl)-piperazin-1-yl]-propyl}-amine

HRID 2167072Notes

Reaction equation

HRID 2167072 reaction equation
NCCCN1CCN(CCCNC2NC3C=CC=CC=3N=2)CC1.C([N:28]([CH2:56][CH:57]([CH3:59])[CH3:58])[CH2:29][CH2:30][CH2:31][N:32]1[CH2:37][CH2:36][N:35]([CH2:38][CH2:39][CH2:40][NH:41][C:42]([NH:44][C:45]2[CH:50]=[CH:49][C:48](OC)=[CH:47][C:46]=2[N+:53]([O-])=O)=S)[CH2:34][CH2:33]1)C(C)C.C(Cl)Cl.C(N(CC)CC)C.[BH4-].[Na+]>O>[NH:44]1[C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=2[N:53]=[C:42]1[NH:41][CH2:40][CH2:39][CH2:38][N:35]1[CH2:36][CH2:37][N:32]([CH2:31][CH2:30][CH2:29][NH:28][CH2:56][CH:57]([CH3:59])[CH3:58])[CH2:33][CH2:34]1

Participants

7

Reactant 5

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 67412597[3-[4-(3-Amino-propyl)-piperazin-1-yl]-propyl]-(1H-benzimidazol-2-yl)-amineHCID 873887991-{3-[4-(3-Diisobutylamino-propyl)-piperazin-1-yl]-propyl}-3-(4-methoxy-2-nitro-phenyl)-thiourea

Product 1

HCID 11675155(1h-Benzimidazol-2-yl)-{3-[4-(3-isobutylamino-propyl)-piperazin-1-yl]-propyl}-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of [3-[4-(3-Amino-propyl)-piperazin-1-yl]-propyl]-(1H-benzimidazol-2-yl)-amine (Intermediate of example 44) (130 mg, 0.41 mmol) in CH2Cl2 (4 mL) isobutyraldehyde (62 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: 90/10/1.2).

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: 90/10/1.2)

Sources & evidence

ORD record
ord-6c29539e07fa499498db016ae46adf94
Source dataset
uspto-grants-2015_06
Patent number
US09044478B2

Reaction notes

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