Water → HCID 59275285, compound

HRID 555114Notes

Reaction equation

HRID 555114 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:20]=[CH:19][C:18]([C:21]4[CH:22]=[C:23]([CH:33]=[CH:34][C:35]=4[CH3:36])[C:24]([NH:26][C:27]4([C:30](O)=[O:31])[CH2:29][CH2:28]4)=[O:25])=[CH:17][C:11]=3[C:12]=2[C:13](=[O:16])[NH:14][CH3:15])=[CH:4][CH:3]=1.[NH:37]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[NH2:38].C(N(CC)C(C)C)(C)C.O>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:20]=[CH:19][C:18]([C:21]4[CH:22]=[C:23]([CH:33]=[CH:34][C:35]=4[CH3:36])[C:24]([NH:26][C:27]4([C:30]([NH:38][NH:37][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])=[O:31])[CH2:28][CH2:29]4)=[O:25])=[CH:17][C:11]=3[C:12]=2[C:13](=[O:16])[NH:14][CH3:15])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 70091tert-Butyl carbazateHCID 81531DiisopropylethylamineHCID 59275421HCID 59275421, compound

Product 1

HCID 59275285HCID 59275285, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1-(3-(2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-5-yl)-4-methylbenzamido)cyclopropanecarboxylic acid (41.6 mg, 0.086 mmol), tert-butyl hydrazinecarboxylate (16.95 mg, 0.128 mmol) and 2-(1H-benzo[d][1,2,3]triazol-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborate (54.9 mg, 0.171 mmol) in DMF (1 mL) at r.t under N2 was added N,N-diisopropylethylamine (0.060 mL, 0.342 mmol). The mixture was stirred at r.t. for 19 hours. The mixture was added 5 ml H2O. The white precipitates were filtered, washed with 3×2 ml H2O and dried (33.1 mg), and was used without further purification. HPLC method: Solvent A=10% MeOH-90% H2O-0.1% TFA, Solvent B=90% MeOH-10% H2O-0.1% TFA, Start % B=0, Final % B=100, Gradient time=2 min, Stop time=3 min, Flow Rate=5 ml/min, Column: PHENOMENEX® Luna, 3.0×50 mm, S10; HPLC Rt=1.750 min.

Workup

  1. customThe white precipitates
  2. filtrationwere filtered
  3. washwashed with 3×2 ml H2O
  4. customdried (33.1 mg)
  5. customwas used without further purification
  6. customB=100, Gradient time=2 min
  7. customtime=3 min, Flow Rate=5 ml/min, Column

Sources & evidence

ORD record
ord-7cc2f73f7ec84314b8859549d4e862e1
Source dataset
uspto-grants-2011_11
Patent number
US08048887B2

Reaction notes

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