Benzenemethanamine, 3-chloro- → HCID 53698366, compound

HRID 1953449Notes

Reaction equation

HRID 1953449 reaction equation
[OH:1][CH:2]([C@@H:6]([NH:11][C:12]([C:14]1([NH:20][C:21]([N:23]2[CH2:28][CH2:27][N:26]([C:29](=[O:31])[CH3:30])[CH2:25][CH2:24]2)=[O:22])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:13])[CH2:7][CH2:8][CH2:9][CH3:10])[C:3](O)=[O:4].ClC1[CH:34]=[C:35]([CH:38]=[CH:39][CH:40]=1)[CH2:36][NH2:37].C1(CN)CCCC1>>[CH:35]1([CH2:36][NH:37][C:3](=[O:4])[C:2](=[O:1])[C@@H:6]([NH:11][C:12]([C:14]2([NH:20][C:21]([N:23]3[CH2:24][CH2:25][N:26]([C:29](=[O:31])[CH3:30])[CH2:27][CH2:28]3)=[O:22])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[O:13])[CH2:7][CH2:8][CH2:9][CH3:10])[CH2:34][CH2:40][CH2:39][CH2:38]1

Participants

4

Reactant 3

HCID 77802Benzenemethanamine, 3-chloro-HCID 80153CyclopentanemethylamineHCID 11690738HCID 11690738, compound

Product 1

HCID 53698366HCID 53698366, compoundYield 11%

Procedure

The same procedure as in Example 28 was repeated except that the (2RS,3S)-2-hydroxy-3-[1-[N-[N-(morpholine-4-carbonyl)amino]cyclohexanecarbonyl]amino]heptanoic acid was replaced by 881 mg of (2RS,3S)-2-hydroxy-3-[N-[1-[N-(4-acetylpiperazine-1-carbonyl)amino]cyclohexanecarbonyl]amino]heptanoic acid synthesized in Reference Example 28 and the 3-chlorobenzylamine was replaced by 496 mg of cyclopentylmethylamine, whereby 64 mg of the captioned N-[(S)-1-(N-cyclopentylmethylamino)-1,2-dioxo-3-heptyl]-1-[N-(4-acetylpiperazine-1-carbonyl) amino]cyclohexanecarboxamide was obtained in a yield of 11%.

Workup

  1. customsynthesized in Reference Example 28

Sources & evidence

ORD record
ord-d56556f01828462d801ee3fe95dce1cf
Source dataset
uspto-grants-2000_09
Patent number
US06117870

Reaction notes

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