1,2-Dichloroethane → N-(2-(1H-indol-3-yl)ethyl)-3,4,5-tris(benzyloxy)benzamide

HRID 1398724Notes

Reaction equation

HRID 1398724 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:12](O)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:35][CH2:36][CH2:37][C:38]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[NH:40][CH:39]=1.C(Cl)CCl.CO>C(Cl)(Cl)Cl>[NH:40]1[C:41]2[C:46](=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:38]([CH2:37][CH2:36][NH:35][C:12](=[O:13])[C:11]2[CH:15]=[C:16]([O:26][CH2:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:17]([O:18][CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:10]=2)=[CH:39]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 887MethanolHCID 67652Tryptamine hydrochlorideHCID 111339693,4,5-Tris(benzyloxy)benzoic Acid

Product 1

HCID 66803725N-(2-(1H-indol-3-yl)ethyl)-3,4,5-tris(benzyloxy)benzamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2d was synthesized the condensation of 3, 4, 5-tris(benzyloxy)benzoic acid (480 mg, 1.09 mmol) and tryptamine hydrochloride (256 mg, 1.308 mmol) using standard EDC coupling method. 2d was isolated as white solid (482 mg, 76%) by elution with 0.5% methanol in chloroform. Rf: 0.538 (1.5% methanol in chloroform); mp: 105-107° C.; IR (neat) νmax 3413.77, 1637.45, 1579.59, 1496.66; 1H NMR (300 MHz, CDCl3) δ 2.96 (t, J=6.14 Hz, 2H), 3.63 (t, J=6.2 Hz, 2H), 4.89 (s, 4H), 4.96 (s, 2H), 6.08 (bs, 1H), 6.85 (S, 3H), 6.87-7.25 (m 18H), 7.54 (d, J=7.5 Hz, 1H), 8.21 (bs, 1H); 13C NMR (75 MHz, CDCl3) δ 24.90, 40.65, 71.01 (2C), 75.05, 106.44 (2C), 111.39, 118.48, 119.36, 121.98, 122.30, 126.86, 127.44 (6C), 127.88, 128.09, 128.40 (6C), 128.48, 129.97, 136.33, 136.56 (2C), 137.31, 140.69, 140.92, 152.54 (2C), 167.12; MS (ESI) m/z calcd. for C38H34N2O4: 582.25. found: 605.07 [M+Na]+.

Workup

  1. custom2d was synthesized

Sources & evidence

ORD record
ord-f1e1ff62f1634703b990d83a51c7e605
Source dataset
uspto-grants-2014_12
Patent number
US08901317B2

Reaction notes

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