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Thiourea → n-[4-({2-[(3-Tert-butylphenyl)amino]-1-methyl-1h-benzimidazol-5-yl}oxy)pyridin-2-yl]-n'-(2-morpholin-4-ylethyl)urea

HRID 1963713
Notes
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Reaction equation

HRID 1963713 reaction equation
[N-]=[C:2]=S.[C:4]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)([CH3:7])([CH3:6])[CH3:5].[NH2:14][C:15]1[CH:16]=[C:17]([CH:37]=[CH:38][C:39]=1NC)[O:18][C:19]1[CH:24]=[CH:23][N:22]=[C:21]([NH:25][C:26]([NH:28][CH2:29][CH2:30][N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)=[O:27])[CH:20]=1.[NH2:42][C:43]([NH2:45])=S>CO>[C:4]([C:8]1[CH:13]=[C:12]([NH:42][C:43]2[N:45]([CH3:2])[C:39]3[CH:38]=[CH:37][C:17]([O:18][C:19]4[CH:24]=[CH:23][N:22]=[C:21]([NH:25][C:26]([NH:28][CH2:29][CH2:30][N:31]5[CH2:32][CH2:33][O:34][CH2:35][CH2:36]5)=[O:27])[CH:20]=4)=[CH:16][C:15]=3[N:14]=2)[CH:11]=[CH:10][CH:9]=1)([CH3:7])([CH3:6])[CH3:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 2723790ThioureaHCID 69006155n-{4-[3-Amino-4-(methylamino)phenoxy] (2-pyridyl)}[(2-morpholin-4-ylethyl)amino]carboxamideHCID 178440816HCID 178440816, compound

Product 1

HCID 59790199n-[4-({2-[(3-Tert-butylphenyl)amino]-1-methyl-1h-benzimidazol-5-yl}oxy)pyridin-2-yl]-n'-(2-morpholin-4-ylethyl)urea

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Procedure

To 3-(tert-butyl)benzenisothiocyanate (1 eq) in methanol was added N-{4-[3-amino-4-(methylamino)phenoxy] (2-pyridyl)}[(2-morpholin-4-ylethyl)amino]carboxamide (1 eq) and the resulting mixture was stirred at ambient temperature for 16 h. LC MS showed formation of corresponding thiourea. To this was added anhydrous ferric chloride (1.5 eq) and stirred for 3 h. The reaction mixture was then concentrated to half its volume and brought to neutral pH with 1N sodium hydroxide. It was then extracted with ethyl acetate and the organic layer was washed with brine and dried with sodium sulfate. The crude material was then purified on preparative chromatography to yield N-[4-({2-[(3-tert-butylphenyl)amino]-1-methyl-1H-benzimidazol-5-yl}oxy)pyridin-2-yl]-N′-(2-morpholin-4-ylethyl)urea. MS: MH+=544.

Workup

  1. stirringstirred for 3 h
  2. concentrationThe reaction mixture was then concentrated to half its volume
  3. extractionIt was then extracted with ethyl acetate
  4. washthe organic layer was washed with brine
  5. dry with materialdried with sodium sulfate
  6. customThe crude material was then purified on preparative chromatography

Sources & evidence

ORD record
ord-9f0ea661367d4946875285155f636d03
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08415382B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes