Sulfuric Acid → 3-[4-(4-Methylpiperazin-1-yl)-phenyl]-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carboxylic acid dimethylamide

HRID 1888546Notes

Reaction equation

HRID 1888546 reaction equation
C[CH2:2][N:3](C(C)C)[CH:4](C)C.[CH3:10][N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:38]=[N:37][C:26]4[NH:27][C:28]5[CH:33]=[N:32][C:31]([C:34](O)=[O:35])=[CH:30][C:29]=5[C:25]=4[CH:24]=3)=[CH:19][CH:18]=2)[CH2:13][CH2:12]1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.Cl.CNC.S(=O)(=O)(O)O>CN(C=O)C>[CH3:2][N:3]([CH3:4])[C:34]([C:31]1[N:32]=[CH:33][C:28]2[NH:27][C:26]3[N:37]=[CH:38][C:23]([C:20]4[CH:21]=[CH:22][C:17]([N:14]5[CH2:13][CH2:12][N:11]([CH3:10])[CH2:16][CH2:15]5)=[CH:18][CH:19]=4)=[CH:24][C:25]=3[C:29]=2[CH:30]=1)=[O:35]

Participants

8

Reactant 6

HCID 1118Sulfuric AcidHCID 10473Dimethylamine, hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine2×HCID 2724699PyBOPHCID 582665593-[4-(4-Methylpiperazin-1-Yl)phenyl]-9h-Pyrrolo[2,3-B:5,4-C']dipyridine-6-Carboxylic Acid

Product 1

HCID 582663793-[4-(4-Methylpiperazin-1-yl)-phenyl]-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carboxylic acid dimethylamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DIPEA (14 μL, 77 μmol) was added to a solution of 3-[4-(4-methylpiperazin-1-yl)-phenyl]-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carboxylic acid (20.0 mg, 51.6 mop, PyBOP (28.2 mg, 54.2 μmol) and HOBt (8.4 mg, 62 μmol) in DMF (0.6 mL). After 10 min at ambient temperature, dimethylamine hydrochloride (20.0 mg, 0.258 mmol) and DIPEA (45 μL, 0.26 mmol) were added to the reaction mixture. After 30 min the reaction mixture was acidified with 10% aqueous sulfuric acid, the solid removed by filtration and the resultant filtrate was purified by preparative HPLC (0-30% MeCN over 30 min, 35 mL/min) to afford the title compound. 1H NMR (DMSO-D6, 400 MHz): 12.40 (s, 1H), 9.03 (m, 1H), 8.92 (m, 1H), 8.89 (m, 1H), 8.55 (m, 1H), 7.75 (d, J=8.9 Hz, 2H), 7.18 (d, J=8.9 Hz, 2H), 3.97 (d, J=12.2 Hz, 2H), 3.56 (d, J=12.2 Hz, 2H), 3.21 (m, 2H), 3.08 (m, 6H), 3.02 (m, 2H), 2.98 (s, 3H). LCMS (Method D): RT=6.19 min, M+H+=415.

Workup

  1. customthe solid removed by filtration
  2. customthe resultant filtrate was purified by preparative HPLC (0-30% MeCN over 30 min, 35 mL/min)

Sources & evidence

ORD record
ord-4ec3a8c0365e41ef8ea7bc51e499c665
Source dataset
uspto-grants-2013_08
Patent number
US08501765B2

Reaction notes

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