Hydrochloric Acid → HCID 57392614, compound

HRID 2036725Notes

Reaction equation

HRID 2036725 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([S:6]([C:9]2[CH:17]=[CH:16][C:15]3[N:14]([CH3:18])[C:13]4[CH2:19][CH:20]5[NH:24][CH:23]([C:12]=4[C:11]=3[C:10]=2C(OC(C)(C)C)=O)[CH2:22][CH2:21]5)(=[O:8])=[O:7])=[CH:2]1.Cl>C(OCC)C>[S:1]1[CH:5]=[CH:4][C:3]([S:6]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH3:18])[C:13]2[CH2:19][CH:20]4[NH:24][CH:23]([C:12]3=2)[CH2:22][CH2:21]4)(=[O:8])=[O:7])=[CH:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67085203HCID 67085203, compound

Product 1

HCID 57392614HCID 57392614, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The product of step A was subjected to Boc-deprotection with 2 M HCl in diethyl ether following the procedure of Example 28, step B. The crude material was purified by flash column chromatography (SiO2, 88:12 chloroform/methanol) to give 2-(3-thienyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole (84 mg, 83%) as a yellow solid: 1H NMR (CDCl3, 300 MHz) δ 8.18 (d, J=1.8 Hz, 1H), 8.00-8.05 (m, 1H), 7.68 (dd, J=8.7, 1.8 Hz, 1H), 7.28-7.35 (m, 3H), 4.60 (d, J=5.1 Hz, 1H), 4.05-4.15 (m, 1H), 3.60 (s, 3H), 3.17 (dd, J=16.5, 4.5 Hz, 1H), 2.53 (d, J=16.5 Hz, 1H), 1.95-2.29 (m, 3H), 1.51-1.65 (m, 1H).

Workup

  1. customThe crude material was purified by flash column chromatography (SiO2, 88:12 chloroform/methanol)

Sources & evidence

ORD record
ord-6951cca727ff495fba72531dcae498bd
Source dataset
uspto-grants-2013_11
Patent number
US08575186B2

Reaction notes

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