4-Amino-6-chloro-1,3-benzenedisulfonamide → (cis)-4-[4-[[7-(aminosulfonyl)-6-chloro-3,4-dihydro-1,1-dioxo-2H-1,2,4-benzothiadiazin-3-yl]methyl]phenoxy]-1-[[(3-ethoxy-3-oxopropyl)ethylamino]carbonyl]-L-proline, phenylmethyl ester

HRID 485332Notes

Reaction equation

HRID 485332 reaction equation
CO[CH:3]=[CH:4][C:5]1[CH:38]=[CH:37][C:8]([O:9][C@@H:10]2[CH2:14][N:13]([C:15]([N:17]([CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:18][CH3:19])=[O:16])[C@H:12]([C:27]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[O:28])[CH2:11]2)=[CH:7][CH:6]=1.[NH2:39][C:40]1[CH:45]=[C:44]([Cl:46])[C:43]([S:47]([NH2:50])(=[O:49])=[O:48])=[CH:42][C:41]=1[S:51]([NH2:54])(=[O:53])=[O:52]>C(#N)C>[NH2:50][S:47]([C:43]1[C:44]([Cl:46])=[CH:45][C:40]2[NH:39][CH:3]([CH2:4][C:5]3[CH:6]=[CH:7][C:8]([O:9][C@@H:10]4[CH2:14][N:13]([C:15]([N:17]([CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:18][CH3:19])=[O:16])[C@H:12]([C:27]([O:29][CH2:30][C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)=[O:28])[CH2:11]4)=[CH:37][CH:38]=3)[NH:54][S:51](=[O:52])(=[O:53])[C:41]=2[CH:42]=1)(=[O:48])=[O:49]

Participants

4

Reactant 2

HCID 671364-Amino-6-chloro-1,3-benzenedisulfonamideHCID 131714306(cis)-4-[4-(2-methoxyethenyl)phenoxy]-1-[[(3-ethoxy-3-oxopropyl)ethylamino]carbonyl]-L-proline, phenylmethyl ester

Product 1

HCID 131714307(cis)-4-[4-[[7-(aminosulfonyl)-6-chloro-3,4-dihydro-1,1-dioxo-2H-1,2,4-benzothiadiazin-3-yl]methyl]phenoxy]-1-[[(3-ethoxy-3-oxopropyl)ethylamino]carbonyl]-L-proline, phenylmethyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

The diphenylmethyl ester product from part (c) in acetonitrile is reacted with a solution of 4-amino-6-chloro-1,3-benzenedisulfonamide in acetonitrile according to the procedure of 1(c) to give (cis)-4-[4-[[7-(aminosulfonyl)-6-chloro-3,4-dihydro-1,1-dioxo-2H-1,2,4-benzothiadiazin-3-yl]methyl]phenoxy]-1-[[(3-ethoxy-3-oxopropyl)ethylamino]carbonyl]-L-proline, phenylmethyl ester.

Sources & evidence

ORD record
ord-b27f5df39e9c47f89cf78463eb12c526
Source dataset
uspto-grants-1985_08
Patent number
US04536501

Reaction notes

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