Pyrrolidine → (R)-7-Cyano-2,3,4,5-tetrahydro-1-(1H-imidazol-4-ylmethyl)-3-(phenylmethyl)-4-[[2-(1 pyrrolidinyl)ethyl]sulfonyl]-1H-1,4-benzodiazepine, dihydrochloride

HRID 849414Notes

Reaction equation

HRID 849414 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[N:12]([CH2:13][C:14]3[N:15]=[CH:16][N:17](C(OC(C)(C)C)=O)[CH:18]=3)[CH2:11][C@@H:10]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:9]([S:33]([CH3:36])(=[O:35])=[O:34])[CH2:8][C:7]=2[CH:37]=1)#[N:2].N1CCCC1.[ClH:43].Cl.Cl.N1C=C(CN2C3C=CC([C:63]4[CH:64]=[N:65][CH:66]=[CH:67][CH:68]=4)=CC=3CN(C(=O)C(F)(F)F)C(CC3C=CC=CC=3)C2)N=C1>>[ClH:43].[ClH:43].[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[N:12]([CH2:13][C:14]3[N:15]=[CH:16][NH:17][CH:18]=3)[CH2:11][C@@H:10]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:9]([S:33]([CH2:36][CH2:64][N:65]3[CH2:63][CH2:68][CH2:67][CH2:66]3)(=[O:34])=[O:35])[CH2:8][C:7]=2[CH:37]=1)#[N:2]

Participants

4

Reactant 3

HCID 31268PyrrolidineHCID 69841490(R)-7-cyano-2,3,4,5-tetrahydro-1-[(((1,1-dimethylethoxy)-carbonyl)-1H-imidazol-4-yl)methyl]-4-(methylsulfonyl)-3-(phenylmethyl)-1H-1,4-benzodiazepineHCID 178478619HCID 178478619, compound

Product 1

HCID 178478682(R)-7-Cyano-2,3,4,5-tetrahydro-1-(1H-imidazol-4-ylmethyl)-3-(phenylmethyl)-4-[[2-(1 pyrrolidinyl)ethyl]sulfonyl]-1H-1,4-benzodiazepine, dihydrochlorideYield 46%

Procedure

Example 327 was prepared in 46% yield as a light yellow solid from Compound A of Example 250 and pyrrolidine as described for Compound B of Example 250. MS (M+H)+ =505.

Sources & evidence

ORD record
ord-c1df14688adb4e5ba73694c9ac95ecd4
Source dataset
uspto-grants-2000_01
Patent number
US06011029

Reaction notes

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