Ethylenediamine → HCID 10340887, compound

HRID 1725873Notes

Reaction equation

HRID 1725873 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]=1[C:22]([OH:24])=[O:23])(=[O:10])=[O:9].[CH2:25]([NH2:28])[CH2:26]N.[CH3:29][N:30](C)C=O>>[NH2:30][CH2:29][CH2:26][CH2:25][NH:28][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]=1[C:22]([OH:24])=[O:23])(=[O:10])=[O:9]

Participants

4

Reactant 3

HCID 3301EthylenediamineHCID 6228DimethylformamideHCID 68862802HCID 68862802, compound

Product 1

HCID 10340887HCID 10340887, compound

Procedure

A mixture of Example 61A (90 mg, 0.22 mmol) in N,N-dimethylformamide (1 mL) was treated with ethylene diamine (1 mL), heated to reflux for 2 days, and dried under vacuum. The concentrate was purified by C18 reverse-phase HPLC with acetonitrile/water/0.1% TFA to provide the desired product. MS (ESI(−)) m/e 398 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 10.53 (s, 1H), 8.05 (m, 1H), 7.96 (dd, 1H), 7.70-7.82 (m, 3H), 7.65 (d, 1H), 7.21-7.51 (m, 4H), 6.73 (d, 1H), 6.57 (t, 1H), 3.01-3.26 (m, 4H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 days
  3. customdried under vacuum
  4. customThe concentrate was purified by C18 reverse-phase HPLC with acetonitrile/water/0.1% TFA

Sources & evidence

ORD record
ord-4d603cf4acec4ea1923909dc8846c474
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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