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3-Amino-5-methylisoxazole → 1-Oxo-N-(3-phenyl-1,2-oxazol-5-yl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]benzimidazole-8-carboxamide

HRID 1521757
Notes
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Reaction equation

HRID 1521757 reaction equation
[O:1]=[C:2]1[C:8]2=[N:9][C:10]3[CH:15]=[CH:14][C:13]([C:16]([OH:18])=O)=[CH:12][C:11]=3[N:7]2[CH2:6][CH2:5][CH2:4][NH:3]1.C(N1C=CN=C1)([N:21]1C=CN=C1)=O.C[C:32]1[O:36][N:35]=[C:34](N)[CH:33]=1.[CH2:38]1[CH2:48][CH2:47]N2[C:41](=NCCC2)[CH2:40][CH2:39]1>C1COCC1>[O:1]=[C:2]1[C:8]2=[N:9][C:10]3[CH:15]=[CH:14][C:13]([C:16]([NH:21][C:32]4[O:36][N:35]=[C:34]([C:38]5[CH:39]=[CH:40][CH:41]=[CH:47][CH:48]=5)[CH:33]=4)=[O:18])=[CH:12][C:11]=3[N:7]2[CH2:6][CH2:5][CH2:4][NH:3]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 661723-Amino-5-methylisoxazoleHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 672364761-Oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]benzimidazole-8-carboxylic acid2×

Product 1

HCID 683226701-Oxo-N-(3-phenyl-1,2-oxazol-5-yl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]benzimidazole-8-carboxamide
Yield 15.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]benzimidazole-8-carboxylic acid (Intermediate B, 71 mg, 0.29 mmol) and 1,1′-carbonyldiimidazole (117 mg, 0.72 mmol) in THF (10 mL) is heated to 60° C. for 1 h. The solution is cooled to room temperature and 5-methyl-3-aminoisoxazole (191 mg, 1.16 mmol) is added. After 10 min DBU (0.11 mL, 0.72 mmol) is added and the mixture heated at 60° C. for 16 h. The solvent is evaporated and H2O is added to the residue. The resulting solid is collected by filtration and is purified via preparative HPLC to afford the title compound (17 mg, 12%).

Workup

  1. temperaturethe mixture heated at 60° C. for 16 h
  2. customThe solvent is evaporated
  3. additionH2O is added to the residue
  4. filtrationThe resulting solid is collected by filtration
  5. customis purified via preparative HPLC

Sources & evidence

ORD record
ord-d00844fc9eae48cdb4ae60ac5c475ce5
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09073926B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes