Dimethylformamide → HCID 46832442, compound

HRID 2410665Notes

Reaction equation

HRID 2410665 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=2)[CH:7]=[C:8]2[C:16]=1[NH:15][C:14]1[CH:13]=[CH:12][C:11]([C:17]([OH:19])=O)=[CH:10][C:9]2=1)(=[O:3])[NH2:2].CN(C(ON1N=N[C:38]2[CH:39]=[CH:40][CH:41]=[N:42][C:37]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:52][N:53](C=O)[CH3:54]>CO>[Cl:27][C:22]1[CH:21]=[C:20]([C:6]2[CH:5]=[C:4]([C:1]([NH2:2])=[O:3])[C:16]3[NH:15][C:14]4[C:9]([C:8]=3[CH:7]=2)=[CH:10][C:11]([C:17]([N:42]2[CH2:37][CH2:38][CH:39]([N:53]([CH3:54])[CH3:52])[CH2:40][CH2:41]2)=[O:19])=[CH:12][CH:13]=4)[CH:25]=[CH:24][C:23]=1[Cl:26]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66604433HCID 66604433, compound

Product 1

HCID 46832442HCID 46832442, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 8-carbamoyl-6-(3,4-dichlorophenyl)-9H-carbazole-3-carboxylic acid (20 mg, 0.05 mmol), HATU (22 mg, 0.06 mmol) and N,N′-diisopropylamine (12 mg, 0.15 mmol) in DMF (0.2 ml) was agitated for 16 h at room temperature. The reaction mixture was diluted with methanol and then purified by reverse phase preparative HPLC to give 16 mg of 3-(3,4-dichlorophenyl)-6-(4-(dimethylamino)piperidine-1-carbonyl)-9H-carbazole-1-carboxamide. MS (ESI) m/z 510.2 (M+H). 1H NMR (DMSO-d6) δ ppm 11.66 (s, 1H), 8.91 (d, 1H, J=1.2), 8.42 (b, 1H), 8.38 (m, 2H), dd, 8.24 (d, 1H, J=2.3), 7.96 (dd, 1H, J=2.3, 8.4), 7.78 (d, 1H, J=8.3), 7.77 (d, 1H, J=8.3), 7.64 (b, 1H), 7.47 (dd, 1H, J=1.7, 8.4), 4.6-3.7 (b, 2H), 3.15-2.85 (b, 2H), 2.55-2.40 (b, 1H), 2.25 (bs, 6H), 1.9-1.7 (b, 2H), 1.47-1.35 (b, 2H).

Workup

  1. custompurified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-05bfb0ee56f14103a5a9f70ca8f6ad1c
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

Loading…