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3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylic acid → 1-(6-methoxy-3,4-dihydro-2H-1-thia-9-aza-phenanthren-3-ylmethyl)-4-[(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carbonyl)-amino]-pyrrolidine-2-carboxylic acid methyl ester

HRID 633832
Notes
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Reaction equation

HRID 633832 reaction equation
Br[CH2:2][CH:3]1[CH2:16][C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH3:18])[CH:13]=3)[N:8]=[CH:7][C:6]=2[S:5][CH2:4]1.[CH3:19][O:20][C:21]([CH:23]1[CH2:27][CH:26]([NH2:28])[CH2:25][N:24]1C(OC(C)(C)C)=O)=[O:22].[O:36]=[C:37]1[NH:42][C:41]2[CH:43]=[C:44]([C:47](O)=[O:48])[CH:45]=[CH:46][C:40]=2[S:39][CH2:38]1>>[CH3:19][O:20][C:21]([CH:23]1[CH2:27][CH:26]([NH:28][C:47]([C:44]2[CH:45]=[CH:46][C:40]3[S:39][CH2:38][C:37](=[O:36])[NH:42][C:41]=3[CH:43]=2)=[O:48])[CH2:25][N:24]1[CH2:2][CH:3]1[CH2:16][C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH3:18])[CH:13]=3)[N:8]=[CH:7][C:6]=2[S:5][CH2:4]1)=[O:22]
ParticipantsProcedureSources & evidenceReaction notes

Participants

4

Reactant 3

HCID 7609933-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylic acidHCID 49130641-Tert-butyl 2-methyl 4-aminopyrrolidine-1,2-dicarboxylateHCID 867307113-bromomethyl-6-methoxy-3,4-dihydro-2H-1-thia-9-aza-phenanthrene

Product 1

HCID 711188941-(6-methoxy-3,4-dihydro-2H-1-thia-9-aza-phenanthren-3-ylmethyl)-4-[(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carbonyl)-amino]-pyrrolidine-2-carboxylic acid methyl ester

Procedure

The titled compound is prepared as an orange viscous oil following Scheme 1 and in analogy to Example 1 using 3-bromomethyl-6-methoxy-3,4-dihydro-2H-1-thia-9-aza-phenanthrene, 4-amino-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester and 3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carboxylic acid as starting material.

Sources & evidence

ORD record
ord-52b482dc85ec4f39935a7dd782bed7e7
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09321788B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes