Triethylamine → HCID 178477735, compound

HRID 1725170Notes

Reaction equation

HRID 1725170 reaction equation
[C:1]12([C:11]3[N:12]([CH2:22][C:23]([NH:25][C:26]([NH2:28])=[NH:27])=[O:24])[C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:14][CH:15]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C(N(CC)CC)C.[CH2:36]([S:38](Cl)(=[O:40])=[O:39])[CH3:37]>C(Cl)Cl>[C:1]12([C:11]3[N:12]([CH2:22][C:23](/[N:25]=[C:26](/[NH2:28])\[NH:27][S:38]([CH2:36][CH3:37])(=[O:40])=[O:39])=[O:24])[C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:14][CH:15]=3)[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 178513098HCID 178513098, compound

Product 1

HCID 178477735HCID 178477735, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1 equivalent of N-[2-(2-adamantan-1-yl-5-phenyl-pyrrol-1-yl)-acetyl]-guanidine in 2.0 mL CH2Cl2 was cooled to 7° C. To the solution 1.0 equivalent of triethylamine was added. The reaction was stirred for 10-15 minutes, after which time ethylsulfonyl chloride was added. The reaction was concentrated and the residue is dissolved in a mixture of DMSO, MeOH and water (1.5 mL total) and purified by Gilson preparative HPLC system. HPLC conditions: YMC Pro C18 column, 20 mm×50 mm ID, 5 uM; 2 mL injection; Solvent A: Water (0.05% NH4OH buffer); Solvent B: acetonitrile (0.05% NH4OH buffer); Gradient: Time 0: 5% B; 2 min: 5% B; 12 min: 95% b, Hold 95% B 3 min; Flow rate 22.5 mL/min; Detection: 254 nm DAD. [M+H] 469, retention time 2.7 min.

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutionthe residue is dissolved in a mixture of DMSO, MeOH and water (1.5 mL total)
  3. custompurified by Gilson preparative HPLC system
  4. custom2 min
  5. custom12 min
  6. custom95% B 3 min

Sources & evidence

ORD record
ord-518a04e965ab40b1a7ffe18d88f2ec73
Source dataset
uspto-grants-2009_02
Patent number
US07488832B2

Reaction notes

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