Potassium Hydroxide → HCID 21955436, compound

HRID 2213154Notes

Reaction equation

HRID 2213154 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[N:15]=[CH:14][C:13]([CH2:16][NH:17][C:18](=[O:41])[CH2:19][N:20]2[C:26](=[O:27])[C:25]3[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=3[CH:23](CC(OC)=O)[C:22]3[CH:37]=[CH:38][CH:39]=[CH:40][C:21]2=3)=[CH:12][CH:11]=1.[OH-:42].[K+].[O:44]1[CH2:49][CH2:48]OCC1.O>>[C:49]([O:44][CH:23]1[C:24]2[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=2[C:26](=[O:27])[N:20]([CH2:19][C:18]([NH:17][CH2:16][C:13]2[CH:14]=[N:15][C:10]([C:2]3[NH:3][C:4]4[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=4[N:1]=3)=[CH:11][CH:12]=2)=[O:41])[C:21]2[CH:40]=[CH:39][CH:38]=[CH:37][C:22]1=2)(=[O:42])[CH3:48]

Participants

4

Reactant 3

HCID 14797Potassium HydroxideHCID 218864351,4-Dioxane--water (1/1)HCID 91245904HCID 91245904, compound

Product 1

HCID 21955436HCID 21955436, compound

Procedure

Methyl {5-[2-({[6-(1H-benzimidazol-2-yl)-3-pyridinyl]methyl}-amino)-2-oxoethyl]-6-oxo-6,11-dihydro-5H-dibenzo[b,e]azepin-11-yl}acetate (1.4 g) was dissolved in 30 ml of 5:1 dioxane/H2O and, after addition of 2.15 eq. of KOH (0.2 g), heated to reflux. After the reaction was complete (12 h), the mixture was evaporated, and the resulting crude product was purified by MPLC (silica gel: Bischoff Prontoprep 60–2540-C18E, 32 μm; eluent: CH3CN/H2O+0.1% acetic acid) and then lyophilized.

Workup

  1. temperatureheated to reflux
  2. custom(12 h)
  3. customthe mixture was evaporated
  4. customthe resulting crude product was purified by MPLC (silica gel: Bischoff Prontoprep 60–2540-C18E, 32 μm; eluent: CH3CN/H2O+0.1% acetic acid)

Sources & evidence

ORD record
ord-895e2449dfc044e2a2a639da48d7e4b2
Source dataset
uspto-grants-2006_09
Patent number
US07105508B1

Reaction notes

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