Water → HCID 68707820, compound

HRID 222105Notes

Reaction equation

HRID 222105 reaction equation
[CH3:1][N:2]1[C:13]2[C:5](=[CH:6][CH:7]=[C:8]3[C:12]=2[CH:11]=[N:10][NH:9]3)[CH:4]=[C:3]1[C:14]([OH:16])=O.C[N:18](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[OH-].[NH4+].O>C(#N)C.C(N(CC)CC)C>[CH3:1][N:2]1[C:13]2[C:5](=[CH:6][CH:7]=[C:8]3[C:12]=2[CH:11]=[N:10][NH:9]3)[CH:4]=[C:3]1[C:14]([NH2:18])=[O:16]

Participants

7

Reactant 4

HCID 962WaterHCID 14923Ammonium HydroxideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68706384HCID 68706384, compound

Product 1

HCID 68707820HCID 68707820, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 1-methyl-1,6-dihydro-1,6,7-triaza-as-indacene-2-carboxylic acid D2 (0.46 mmol) in dry acetonitrile (6 mL) and triethylamine (0.13 mL), first TBTU (2 eq) and, after 10 min, 30% aq ammonium hydroxide solution (2 eq) were added under stirring at rt. After 2 h at rt, the mixture was poured into water and the slurry was extracted with AcOEt. The organic layer was washed with brine, dried (Na2SO4) and concentrated to yield a crude product that was purified by chromatography on silica gel (eluant: MeOH/DCM 1:9). Obtained the title compound (10%). ESI (+) MS: m/z 215 (MH+). 1H NMR: 4.36 (s, 3H), 6.95 (bs, 2H), 7.29 (s, 1H), 7.31 (d, J=8.73, 1H), 7.58 (d, J=8.73, 1H), 8.73 (s, 1H), 13.32 (s, 1H).

Workup

  1. extractionthe slurry was extracted with AcOEt
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customto yield a crude product that
  6. customwas purified by chromatography on silica gel (eluant: MeOH/DCM 1:9)

Sources & evidence

ORD record
ord-d203a8bff7274968a222ce497a32b390
Source dataset
uspto-grants-2012_06
Patent number
US08207180B2

Reaction notes

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