N-bromobutanimide → HCID 178501312, compound

HRID 2053018Notes

Reaction equation

HRID 2053018 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:8][C@@H:7]([N:9]2[C:13]3[N:14]=[CH:15][N:16]=[C:17]([NH2:18])[C:12]=3[C:11]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH:20]=3)=[CH:10]2)[CH2:6]1)=[O:4].[Br:33]N1C(=O)CCC1=O>CN(C)C=O>[CH3:1][O:2][C:3]([C@H:5]1[CH2:6][C@@H:7]([N:9]2[C:13]3[N:14]=[CH:15][N:16]=[C:17]([NH2:18])[C:12]=3[C:11]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:26][C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:20]=3)=[C:10]2[Br:33])[CH2:8]1)=[O:4]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 178501314HCID 178501314, compound

Product 1

HCID 178501312HCID 178501312, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound is prepared in analogy to Example 103 starting from 12.9 g (30.11 mmol) cis-3-[4-amino-5-(3-benzyloxy-phenyl)-pyrrolo[2,3-d]pyrimidin-7-yl]-cyclobutanecarboxylic acid methyl ester (see Step 3.1 above) and 6.07 g (33.12 mmol) N-bromosuccinimide in 250 ml dry N,N-dimethylformamide. After work-up, the raw material is purified by chromatography on silicagel (solvent: hexane-ethyl acetate 1:1). Analytical HPLC: tR=11.85 min (Grad 1); ES-MS: m/eo=506.9 and 509.9; NMR (DMSO-d6): 8.14/s (1H), 7.3-7.5/several m's (6H), 7.09/“d” (1H); 7.05/s (1H); 6.98/“d” (1H); 5.5-6.5/b (NH2); 5.13/s (2H); 5.11/m (1H); 3.66/s (3H); 3.35-3.5/m (2H); 3.08/m (1H); 2.58-2.7/m (2H).

Workup

  1. customAfter work-up, the raw material is purified by chromatography on silicagel (solvent: hexane-ethyl acetate 1:1)

Sources & evidence

ORD record
ord-c2f4d4ceddd84a87956d7804dcddef71
Source dataset
uspto-grants-2008_02
Patent number
US07326699B2

Reaction notes

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