Hydrochloric Acid → HCID 67085230, compound

HRID 2036757Notes

Reaction equation

HRID 2036757 reaction equation
[C:1]1([S:7]([C:10]2[CH:18]=[CH:17][C:16]3[N:15]([CH2:19][CH3:20])[C:14]4[CH2:21][CH:22]5[NH:26][CH:25]([C:13]=4[C:12]=3[C:11]=2C(OC(C)(C)C)=O)[CH2:24][CH2:23]5)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:34]>C(OCC)C>[ClH:34].[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([CH2:19][CH3:20])[C:14]2[CH2:21][CH:22]4[NH:26][CH:25]([C:13]3=2)[CH2:24][CH2:23]4)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67085715HCID 67085715, compound

Product 1

HCID 67085230HCID 67085230, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The product of step B was subjected to Boc-deprotection with 2 M HCl in diethyl ether following the procedure of Example 27, step D. The crude material was purified by flash column chromatography (SiO2, 99:0.9:0.1 to 80:18:2 dichloromethane/methanol/ammonium hydroxide) and semi-preparative HPLC. The free base was dissolved in methanol and treated with an excess of HCl in diethyl ether. The solution was concentrated in vacuo and the residue lyophilized from water/acetonitrile to give 2-phenylsulfonyl-5-ethyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride (28 mg, 100%, AUC HPLC >99%) as a white solid: mp 200-204° C. dec; 1H NMR (CD3OD, 300 MHz) δ 8.28 (d, J=1.8 Hz, 1H), 7.91-7.98 (m, 2H), 7.72 (dd, J=8.7; 1.8 Hz, 1H), 7.49-7.63 (m, 4H), 5.25-5.32 (m, 1H), 4.49-4.58 (m, 1H), 4.10-4.28 (m, 2H), 3.42-3.56 (m, 1H), 3.00-3.11 (m, 1H), 2.23-2.52 (m, 3H), 1.88-2.05 (m, 1H), 1.32 (t, J=7.2 Hz, 3H); ESI MS m/z 367 [M+H]+

Workup

  1. customThe crude material was purified by flash column chromatography (SiO2, 99:0.9:0.1 to 80:18:2 dichloromethane/methanol/ammonium hydroxide) and semi-preparative HPLC
  2. dissolutionThe free base was dissolved in methanol
  3. additiontreated with an excess of HCl in diethyl ether
  4. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-b8d1b9e9a5204f8bbc2c8d4b3604c74c
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

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