4-(2-hydrazinylethyl)morpholine → Formate 4-(2-{5-[(2S,4R)-4-(2-chloro-benzenesulfonyl)-2-(1-cyano-cyclopropylcarbamoyl)-pyrrolidin-1-yl]-3-methyl-pyrazol-1-yl}-ethyl)-morpholin-4-ium

HRID 1697765Notes

Reaction equation

HRID 1697765 reaction equation
CO[C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])(=[O:12])=[O:11])[CH2:7][N:6]1[C:20]1[N:24]([CH2:25][CH2:26][N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[N:23]=[C:22]([CH3:33])[CH:21]=1)=[O:4].ClC1C=CC=CC=1S([C@H]1C[N:47]([C:49](=S)[CH2:50][C:51](=O)[CH3:52])[C@H]([C:55]([O:57]C)=[O:56])C1)(=O)=O.[NH:59](CCN1CCOCC1)N>>[Cl:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[S:10]([C@H:8]1[CH2:7][N:6]([C:20]2[N:24]([CH2:25][CH2:26][NH+:27]3[CH2:28][CH2:29][O:30][CH2:31][CH2:32]3)[N:23]=[C:22]([CH3:33])[CH:21]=2)[C@H:5]([C:3](=[O:4])[NH:59][C:50]2([C:49]#[N:47])[CH2:52][CH2:51]2)[CH2:9]1)(=[O:12])=[O:11].[CH:55]([O-:57])=[O:56]

Participants

4

Reactant 3

HCID 30293944-(2-hydrazinylethyl)morpholineHCID 66772187(2S,4R)-4-(2-Chlorophenylsulfonyl)-1-(3-methyl-1-(2-morpholinoethyl)-1H-pyrazol-5-yl)pyrrolidine-2-carboxylic acid methyl esterHCID 86646820(2S,4R)-methyl 4-(2-chlorophenylsulfonyl)-1-(3-oxobutanethioyl)pyrrolidine-2-carboxylate

Product 1

HCID 67278355Formate 4-(2-{5-[(2S,4R)-4-(2-chloro-benzenesulfonyl)-2-(1-cyano-cyclopropylcarbamoyl)-pyrrolidin-1-yl]-3-methyl-pyrazol-1-yl}-ethyl)-morpholin-4-ium

Procedure

(2S,4R)-4-(2-Chlorophenylsulfonyl)-1-(3-methyl-1-(2-morpholinoethyl)-1H-pyrazol-5-yl)pyrrolidine-2-carboxylic acid methyl ester. In analogy to the procedure described in example 192 h, (2S,4R)-methyl 4-(2-chlorophenylsulfonyl)-1-(3-oxobutanethioyl)pyrrolidine-2-carboxylate (example 253c) was reacted with 4-(2-hydrazinoethyl)morpholine (CAS Reg. No. 2154-24-7) to give the title compound as yellow oil. MS (ESI): m/z=497.3 [M+H]+.

Sources & evidence

ORD record
ord-da4f9e67d4624920ad028838b76ebacb
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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