2-Bromomethyl-1-tert-butoxycarbonyl-5-chloroindole → {[1-(Aminoquinazolin-7-ylmethyl)-2-oxopyrrolidin-3-(S)-yl][3-(5-chlorothiophen-2-yl)allyl]amino}acetic acid methyl ester trifluoroacetate

HRID 651691Notes

Reaction equation

HRID 651691 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:8]([O:12][C:13](=[O:34])[CH2:14][NH:15][C@H:16]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]2[CH:31]=[C:30]3[C:25]([C:26](N)=[N:27][CH:28]=[N:29]3)=[CH:24][CH:23]=2)[C:17]1=[O:33])(C)(C)C.[Cl:35][C:36]1[S:40][C:39]([CH:41]=[CH:42][CH2:43]Br)=[CH:38][CH:37]=1.BrCC1[N:48](C(OC(C)(C)C)=O)C2C(C=1)=CC(Cl)=CC=2>>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:8][O:12][C:13](=[O:34])[CH2:14][N:15]([C@H:16]1[CH2:20][CH2:19][N:18]([CH:21]([NH2:48])[C:22]2[CH:31]=[C:30]3[C:25]([CH:26]=[N:27][CH:28]=[N:29]3)=[CH:24][CH:23]=2)[C:17]1=[O:33])[CH2:43][CH:42]=[CH:41][C:39]1[S:40][C:36]([Cl:35])=[CH:37][CH:38]=1

Participants

4

Reactant 3

HCID 217084992-Bromomethyl-1-tert-butoxycarbonyl-5-chloroindoleHCID 537995313-(5-Chlorothiophen-2-yl)allyl bromideHCID 70081978{[1-(4-aminoquinazolin-7-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]amino}acetic acid tert-butyl ester trifluoroacetate

Product 1

HCID 70121911{[1-(Aminoquinazolin-7-ylmethyl)-2-oxopyrrolidin-3-(S)-yl][3-(5-chlorothiophen-2-yl)allyl]amino}acetic acid methyl ester trifluoroacetate

Procedure

Same procedure as EXAMPLE 103, but using {[1-(4-aminoquinazolin-7-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]amino}acetic acid tert-butyl ester trifluoroacetate instead of 3-(S)-amino-1-(4-aminoquinazolin-7-ylmethyl)pyrrolidin-2-one hydrochloride, and 3-(5-chlorothiophen-2-yl)allyl bromide instead of added 2-bromomethyl-1-tert-butoxycarbonyl-5-chloroindole.

Sources & evidence

ORD record
ord-8ee361fc867949d380effcec4478bac2
Source dataset
uspto-grants-2001_08
Patent number
US06281227B1

Reaction notes

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