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

HRID 1521758
Notes
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Reaction equation

HRID 1521758 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.CN(C([O:26][N:27]1N=N[C:29]2[CH:30]=[CH:31]C=[N:33][C:28]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(P1(N(C)CCCN1)=NC(C)(C)C)CC.CC1ON=C(N)C=1>ClC(Cl)C.CO>[CH3:31][C:30]1[O:26][N:27]=[C:28]([NH:33][C:16]([C:13]2[CH:14]=[CH:15][C:10]3[N:9]=[C:8]4[C:2](=[O:1])[NH:3][CH2:4][CH2:5][CH2:6][N:7]4[C:11]=3[CH:12]=2)=[O:18])[CH:29]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 661723-Amino-5-methylisoxazoleHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 199900182-tert-butylimino-N,N-diethyl-1-methyl-1,3,2lambda5-diazaphosphinan-2-amineHCID 672364761-Oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]benzimidazole-8-carboxylic acid2×

Product 1

HCID 68322629
N-(5-Methyl-1,2-oxazol-3-yl)-1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]benzimidazole-8-carboxamide
Yield 36.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 63651,1-DichloroethaneSolvent

Procedure

A mixture of 1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]benzimidazole-8-carboxylic acid (Intermediate B, 51 mg, 0.21 mmol) and HATU (89 mg, 0.23 mmol) in dichloroethane (3 mL) is stirred at room temperature for 1 h. 2-tert-Butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine on polystyrene (64 mg, 0.64 mmol) is added and the mixture is stirred at room temperature for 10 min. 5-Methyl-3-aminoisoxazole (62 mg, 0.64 mmol) is added and the reaction is stirred at 60° C. for 16 h and is cooled to room temperature. The mixture is diluted with methanol, filtered and evaporated. The residue is purified via flash column chromatography using a gradient elution of 0-10% CH2Cl2/methanol and is triturated with CH2Cl2 (3 mL), filtered and dried to afford the title compound (25 mg, 36%).

Workup

  1. stirringthe mixture is stirred at room temperature for 10 min
  2. stirringthe reaction is stirred at 60° C. for 16 h
  3. temperatureis cooled to room temperature
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is purified via flash column chromatography
  7. washa gradient elution of 0-10% CH2Cl2/methanol
  8. customis triturated with CH2Cl2 (3 mL)
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-9ad5ced1a7aa4dc7b0707d64b2c5aca0
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