HCID 57634154, compound → HCID 23654067, compound

HRID 661033Notes

Reaction equation

HRID 661033 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C@H:11]([NH:27]S(C2C=CC([N+]([O-])=O)=CC=2)(=O)=O)[CH2:12][N:13]([C:21]2[S:22][C:23](Br)=[CH:24][N:25]=2)C(=O)OC(C)(C)C)=[CH:2]1.[O:40]=[C:41]1[NH:45][C:44]2[CH:46]=[CH:47][C:48](B(O)O)=[CH:49][C:43]=2[S:42]1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:27][C@@H:11]([CH2:10][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1)[CH2:12][NH:13][C:21]1[S:22][C:23]([C:48]2[CH:47]=[CH:46][C:44]3[NH:45][C:41](=[O:40])[S:42][C:43]=3[CH:49]=2)=[CH:24][N:25]=1

Participants

4

Reactant 2

HCID 57634154HCID 57634154, compoundHCID 68993557HCID 68993557, compound

Product 1

HCID 23654067HCID 23654067, compound

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

This compound was synthesized using a procedure similar to that shown in Scheme 1 with a coupling reaction between (S)-tert-butyl 3-(1H-indol-3-yl)-2-(4-nitrophenylsulfonamido)propyl(5-bromothiazol-2-yl)carbamate and commercially available 2-oxo-2,3-dihydrobenzo[d]thiazol-6-ylboronic acid using PdCl2(PPh3)2 as the catalyst instead of tetrakis-(triphenylphosphine)palladium. MS m/z: 422 (M+1). 1H NMR (400 MHz, CD3OD): δ ppm 3.11-3.20 (m, 2H), 3.57 (d, J=7.04 Hz, 2H), 3.66-3.72 (m, 1H), 3.76-3.86 (m, 1H), 7.05-7.18 (m, 3H), 7.25 (s, 1H), 7.33-7.42 (m, 3H), 7.52 (d, J=1.56 Hz, 1H), 7.60 (d, J=7.82 Hz, 1H).

Workup

  1. customThis compound was synthesized

Sources & evidence

ORD record
ord-88fe26aa57ff477d996e3bd274833453
Source dataset
uspto-grants-2011_12
Patent number
US08084479B2

Reaction notes

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