Dimethylformamide → 7H-indolo[2,1-a][2]benzazepine-6,10-dicarboxamide

HRID 1453376Notes

Reaction equation

HRID 1453376 reaction equation
[CH:1]1[C:11]2[C:10]3=[CH:12][C:13]4[CH:14]=[CH:15][C:16]([C:19](O)=[O:20])=[CH:17][C:18]=4[N:9]3[CH2:8][CH:7]=[CH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C[N:23](C)S(N)(=O)=O.N=C=N.C[N:33](C)[CH:34]=[O:35]>CN(C1C=CN=CC=1)C>[CH:1]1[C:11]2[C:10]3=[CH:12][C:13]4[CH:14]=[CH:15][C:16]([C:19]([NH2:23])=[O:20])=[CH:17][C:18]=4[N:9]3[CH2:8][C:7]([C:34]([NH2:33])=[O:35])=[CH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 134472N,N-DimethylsulfamideHCID 160435CarbodiimideHCID 666396797H-indolo[2,1-a][2]benzazepine-10-carboxylic acid

Product 1

HCID 688469427H-indolo[2,1-a][2]benzazepine-6,10-dicarboxamide

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a solution of 7H-indolo[2,1-a][2]benzazepine-10-carboxylic acid, 13-cyclohexyl-3-methoxy-6-[[[2-(methylamino)-2-oxoethyl]amino]carbonyl]- (110 mg, 0.22 mmol), N,N-dimethylsulfamide (136 mg, 1.10 mmol) and DMAP (134 mg, 1.10 mmol) in dimethylformamide (2 mL) was added PS-carbodiimide (576 mg, 1.3 mmol/g, 0.88 mmol). The reaction solution was shaken at rt overnight, filtered, concentrated and purified by preparative HPLC (MeOH/H2O with an NH4OAc buffer) to yield 7H-indolo[2,1-a][2]benzazepine-6,10-dicarboxamide, 13-cyclohexyl-N10-[(dimethylamino)sulfonyl]-3-methoxy-N6-[2-(methylamino)-2-oxoethyl]- (40 mg, 0.07 mmol, 30%) as a yellow solid. 1HNMR (500 MHz, CD3OD) δ 8.13 (s. 1H), 7.85 (d, J=8.6 Hz, 1H), 7.60-7.52 (m, 3H), 7.15 (dd, J=2.8, 8.8 Hz, 1H), 7.10 (d, J=2.8 Hz, 1H), 5.64-5.53 (m, 1H), 4.19-4.07 (m, 1H), 3.96-3.86 (m, 2H), 3.91 (s, 3H), 2.99 (s, 6H), 2.89-2.80 (m, 1H), 2.71 (s, 3H), 2.16-1.70 (m, 6H), 1.54-1.16 (m, 4H). LCMS: m/e 606 (M−H)−, ret time 1.57 min, column A, 3 minute gradient.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. custompurified by preparative HPLC (MeOH/H2O with an NH4OAc buffer)

Sources & evidence

ORD record
ord-d1ba69ed357941b0846dd42baced2892
Source dataset
uspto-grants-2009_01
Patent number
US07473688B2

Reaction notes

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