N,N-Dimethylsulfamide → HCID 66844456, compound

HRID 1970943Notes

Reaction equation

[CH:1]1([C:7]2[CH:31]=[CH:30][CH:29]=[C:28]3[C:8]=2[CH:9]=[C:10]2[C:16]4[CH:17]=[C:18]([C:21](O)=[O:22])[CH:19]=[CH:20][C:15]=4[N:14]4[CH2:24][C:25]([CH3:27])=[N:26][C:13]4=[CH:12][N:11]23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:32][N:33]([CH3:38])[S:34]([NH2:37])(=[O:36])=[O:35].CCN=C=NCCCN(C)C.Cl>CN(C=O)C.CN(C1C=CN=CC=1)C.CS(C)=O.CO>[CH:1]1([C:7]2[CH:31]=[CH:30][CH:29]=[C:28]3[C:8]=2[CH:9]=[C:10]2[C:16]4[CH:17]=[C:18]([C:21]([NH:37][S:34]([N:33]([CH3:38])[CH3:32])(=[O:36])=[O:35])=[O:22])[CH:19]=[CH:20][C:15]=4[N:14]4[CH2:24][C:25]([CH3:27])=[N:26][C:13]4=[CH:12][N:11]23)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 10-cyclohexyl-2-methyl-4H-imidazo[1,2-a]indolo[1,2-d][1,4]benzodiazepine-7-carboxylic acid (58 g, 0.14 mmol) and N,N-dimethylsulfamide (82 g, 0.66 mol) in DMF (2 mL) added DMAP (80 mg, 0.66 mmol) and then EDCI-HCl (100 mg, 0.52 mmol). The reaction mixture was stirred at 60° C. for 2 h, cooled to rt, diluted with DMSO and MeOH and purified by prep HPLC (MeOH/H2O with 10 mM TFA buffer) to yield 10-cyclohexyl-N-((dimethylamino)sulfonyl)-2-methyl-4H-imidazo[1,2-a]indolo[1,2-d][1,4]benzodiazepine-7-carboxamide (32 mg, 0.062 mmol, 44%) as a pink solid. 1H NMR (300 MHz, CD3OD) δ 1.14-1.32 (m, 1H), 1.36-1.57 (m, 3H), 1.73-1.85 (m, 2H), 1.94-2.20 (m, 4H), 2.34 (s, 3H), 2.84-2.98 (m, 1H), 3.04 (s, 6H), 5.20 (d, J=16.1 Hz, 1H), 5.97 (d, J=16.1 Hz, 1H), 7.66 (dd, J=8.6, 1.7 Hz, 1H), 7.71 (s, 1H), 7.77-7.90 (m, 4H), 8.01 (d, J=8.8 Hz, 1H), 8.27 (s, 1H). LCMS: m/e 518 (M+H)+, ret time 1.80 min.

Workup

temperaturecooled to rt
custompurified by prep HPLC (MeOH/H2O with 10 mM TFA buffer)

Sources & evidence

ORD record: ord-83218380b33d40178915f5975139b009
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431568B2

Reaction notes

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