2-(1-Benzyl-1H-indol-3-yl)ethan-1-amine--hydrogen chloride (1/1) → HCID 57189842, compound

HRID 2188456Notes

Reaction equation

HRID 2188456 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:10]([NH:12][C@@H:13]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]([O:28]C)=[O:27])=[C:20]([C:30]([O:32]C)=[O:31])[CH:19]=1)[C:14](O)=[O:15])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH2:42]([N:49]1[C:57]2[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=2)[C:51]([CH2:58][CH2:59][NH2:60])=[CH:50]1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>>[CH2:42]([N:49]1[C:57]2[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=2)[C:51]([CH2:58][CH2:59][NH:60][C:14](=[O:15])[C@@H:13]([NH:12][C:10](=[O:11])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]([OH:28])=[O:27])=[C:20]([CH:19]=2)[C:30]([OH:32])=[O:31])=[CH:50]1)[C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1

Participants

3

Reactant 2

HCID 184770512-(1-Benzyl-1H-indol-3-yl)ethan-1-amine--hydrogen chloride (1/1)HCID 57019224(2S)-2-({(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoyl}amino)-3-[3-(methoxycarbonyl)-4-(2-methoxy-2-oxoethoxy)phenyl]propanoic acid

Product 1

HCID 57189842HCID 57189842, compoundYield 48.4%

Procedure

Synthesis was performed from (2S)-2-({(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoyl}amino)-3-[3-(methoxycarbonyl)-4-(2-methoxy-2-oxoethoxy)phenyl]propanoic acid (73 mg, 0.13 mmol) and 2-(1-benzyl-1H-indol-3-yl)ethylamine hydrochloride (45 mg, 0.16 mmol) according to Method C to give the title compound (48 mg). 1H-NMR (400 MHz, CD3OD) d 7.56 (d, J=7.6 Hz, 1H), 6.81 (d, J=8.5 Hz, 1H), 5.28 (s, 2H), 4.69 (s, 2H), 4.48 (m, 1H), 4.22 (dd, J=5.2 Hz, J=9.2 Hz, 1H), 3.52 (m, 1H), 3.38 (m, 1H), 2.98 (m, 2H), 2.86 (m, 3H), 2.72 (dd, J=9.3 Hz, J=13.8 Hz, 1H), 1.33 (s, 9H); HRMS m/z 762.3292 (calc. of monoisotopic mass for C43H46N4O9 gives 762.3265).

Workup

  1. customSynthesis

Sources & evidence

ORD record
ord-3c0d6ac2f0104172b8340593430ee9cb
Source dataset
uspto-grants-2002_06
Patent number
US06410585B1

Reaction notes

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