2-(1-Methyl-2-((pyridin-4-ylmethyl)carbamoyl)hydrazinyl)acetic acid → 1-(2-((S)-1-((benzo[b]thiophen-3-ylmethyl)((S)-1,1-diethoxypropan-2-yl)amino)-1-oxopropan-2-ylamino)-2-oxoethyl)-1-methyl-4-(pyridin-4-ylmethyl)semicarbazide

HRID 718978Notes

Reaction equation

HRID 718978 reaction equation
[CH3:1][N:2]([CH2:14][C:15]([OH:17])=O)[NH:3][C:4](=[O:13])[NH:5][CH2:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1.[NH2:18][C@@H:19]([CH3:42])[C:20]([N:22]([CH2:32][C:33]1[C:34]2[CH:41]=[CH:40][CH:39]=[CH:38][C:35]=2[S:36][CH:37]=1)[C@@H:23]([CH3:31])[CH:24]([O:28][CH2:29][CH3:30])[O:25][CH2:26][CH3:27])=[O:21]>>[S:36]1[CH:37]=[C:33]([CH2:32][N:22]([C@@H:23]([CH3:31])[CH:24]([O:28][CH2:29][CH3:30])[O:25][CH2:26][CH3:27])[C:20](=[O:21])[C@@H:19]([NH:18][C:15](=[O:17])[CH2:14][N:2]([CH3:1])[NH:3][C:4]([NH:5][CH2:6][C:7]2[CH:8]=[CH:9][N:10]=[CH:11][CH:12]=2)=[O:13])[CH3:42])[C:34]2[CH:41]=[CH:40][CH:39]=[CH:38][C:35]1=2

Participants

3

Reactant 2

HCID 533975202-(1-Methyl-2-((pyridin-4-ylmethyl)carbamoyl)hydrazinyl)acetic acidHCID 67075261(S)-2-amino-N-(benzo[b]thiophen-3-ylmethyl)-N-((S)-1,1-diethoxypropan-2-yl)propanamide

Product 1

HCID 670757361-(2-((S)-1-((benzo[b]thiophen-3-ylmethyl)((S)-1,1-diethoxypropan-2-yl)amino)-1-oxopropan-2-ylamino)-2-oxoethyl)-1-methyl-4-(pyridin-4-ylmethyl)semicarbazide

Procedure

According to the procedure described in the synthesis method of Compound II-15, 2-(1-methyl-2-(pyridin-4-ylmethylcarbamoyl)hydrazinyl)acetic acid (Compound VI-6) 98 mg (0.41 mmol) was coupled with (S)-2-amino-N-(benzo[b]thiophen-3-ylmethyl)-N—((S)-1,1-diethoxypropan-2-yl)propanamide (Compound IV-12) 100 mg (0.27 mmol) to obtain the title compound.

Sources & evidence

ORD record
ord-703bae4a21ca4f03b6dc48b8ca8c0e80
Source dataset
uspto-grants-2015_11
Patent number
US09193734B2

Reaction notes

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