N,N-Dimethylsulfamide → HCID 66844373, compound

HRID 1970937Notes

Reaction equation

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

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of 10-cyclohexyl-4H-indolo[1,2-d][1,2,4]triazolo[4,3-a][1,4]benzodiazepine-7-carboxylic acid (50 mg, 0.13 mmol) and N,N-dimethylsulfamide (78 mg, 0.63 mmol) in DMA (2 mL), was added DMAP (77 mg, 0.63 mmol) and then EDCI-HCl (96 mg, 0.50 mmol). The mixture was stirred at 45° C. overnight, diluted with DMSO and MeOH and purified by prep HPLC (MeOH/H2O with 10 mM TFA buffer) to yield 10-cyclohexyl-N-((dimethylamino)sulfonyl)-4H-indolo[1,2-d][1,2,4]triazolo[4,3-a][1,4]benzodiazepine-7-carboxamide (20 mg, 0.040 mmol, 31%) as light pink solid. 1H NMR (500 MHz, CD3OD) δ 1.16-1.26 (m, 1H), 1.39-1.55 (m, 3H), 1.73-1.83 (m, 2H), 1.93-2.22 (m, 4H), 2.86-2.96 (m, 1H), 3.04 (s, 6H), 5.14 (d, J=15.9 Hz, 1H), 6.05 (d, J=15.9 Hz, 1H), 7.66 (dd, J=8.55, 1.5 Hz, 1H), 7.72-7.80 (m, 3H), 7.82-7.87 (m, 1H), 7.99 (d, J=8.5, 1H), 8.34 (s, 1H), 9.08 (s, 1H). LCMS: m/e 505 (M+H)+, ret time 1.94 min.

Workup

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

Sources & evidence

ORD record: ord-4b080380a7d94efba6cec479827cbfbe
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431568B2

Reaction notes

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