N,N-Dimethylsulfamide → HCID 66844712, compound

HRID 1970939Notes

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]([OH:23])=O)[CH:19]=[CH:20][C:15]=4[N:14]4[CH:24]=[N:25][N:26]([CH3:27])[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>CC(N(C)C)=O.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:23])[CH:19]=[CH:20][C:15]=4[N:14]4[CH:24]=[N:25][N:26]([CH3:27])[C:13]4=[CH:12][N:11]23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 10-cyclohexyl-1-methyl-4H-indolo[1,2-d][1,2,4]triazolo[4,3-a][1,4]benzodiazepine-7-carboxylic acid (54 mg, 0.13 mmol) and N,N-dimethylsulfamide (81 mg, 0.65 mmol) in DMA (2 mL), was added DMAP (80 mg, 0.65 mmol), and 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)-1-methyl-4H-indolo[1,2-d][1,2,4]triazolo[4,3-a][1,4]benzodiazepine-7-carboxamide (29 mg, 0.056 mmol, 43%) as a bright yellow solid. 1H NMR (500 MHz, CD3OD) δ 1.22-1.34 (m, 1H), 1.41-1.62 (m, 3H), 1.77-1.85 (m, 2H), 1.95-2.18 (m, 4H), 2.71 (s, 3H), 2.90-3.00 (m, 1H), 3.05 (s, 6H), 5.09 (d, J=15.9 Hz, 1H), 6.03 (d, =15.9 Hz, 1H), 7.67 (dd, J=8.2, 1.5 Hz, 1H), 7.79-7.87 (m, 4H), 8.00 (d, J=8.6 Hz, 1H), 8.33 (s, 1H). LCMS: m/e 519 (M+H)+, ret time 1.96 min.

Workup

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

Sources & evidence

ORD record: ord-f681e7aa05d9484c9857a16d413405b6
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431568B2

Reaction notes

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