1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 58975097, compound

HRID 737058Notes

Reaction equation

HRID 737058 reaction equation
Cl.CN(C)CCCN=C=NCC.[CH:13]1([C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]([S:27]([C:30]3[CH:38]=[CH:37][C:33]([C:34](O)=[O:35])=[CH:32][CH:31]=3)(=[O:29])=[O:28])[CH:19]=2)[CH2:17][CH2:16][CH2:15][CH2:14]1.[CH2:39]([NH2:45])[C@@H:40]1[O:44][CH2:43][CH2:42][CH2:41]1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH:13]1([C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]([S:27]([C:30]3[CH:31]=[CH:32][C:33]([C:34]([NH:45][CH2:39][C@H:40]4[CH2:41][CH2:42][CH2:43][O:44]4)=[O:35])=[CH:37][CH:38]=3)(=[O:28])=[O:29])[CH:19]=2)[CH2:14][CH2:15][CH2:16][CH2:17]1

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2734124(R)-(-)-TetrahydrofurfurylamineHCID 58975136HCID 58975136, compound

Product 1

HCID 58975097HCID 58975097, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Add 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC; 98 mg, 0.51 mmol, 1.5 equiv) and 4-(dimethylamino)pyridine (DMAP; 70 mg, 0.57 mmol, 1.7 equiv) to a solution of 4-(3-cyclopentylindole-1-sulfonyl)benzoic acid (126 mg, 0.341 mmol, 1 equiv) and (R)-(−)-tetrahydrofurfurylamine (Aldrich; 140 μL, 140 mg, 1.4 mmol, 4.0 equiv) in anhydr CH2Cl2 (1 mL). After stirring 16 h, transfer the reaction solution to a column of silica gel (80 mm×20 mm dia.) and elute (10-45% EtOAc/hex) to give 24 mg (16%) of 4-(3-cyclopentylindole-1-sulfonyl)-N—[(R)-1-(tetrahydrofuran-2-yl)methyl]benzamide as a white foam. MS (m/e): 452.96 (M+1); 451.14 (M−1).

Workup

  1. washelute (10-45% EtOAc/hex)

Sources & evidence

ORD record
ord-b4e2831be3594837a36752809366c0bb
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

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