N,N-Dimethylsulfamide → HCID 66844690, compound

HRID 1970941Notes

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][CH: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>CN(C=O)C.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][CH: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: 60 °C

Procedure

To a solution of 10-cyclohexyl-4H-imidazo[1,2-a]indolo[1,2-d][1,4]benzodiazepine-7-carboxylic acid (25 mg, 0.063 mmol) and N,N-dimethylsulfamide (41 mg, 0.33 mmol) in DMF (1.5 mL), was added DMAP (40 mg, 0.33 mmol) and then EDCI-HCl (50 mg, 0.26 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)-4H-imidazo[1,2-a]indolo[1,2-d][1,4]benzodiazepine-7-carboxamide (5.4 mg, 0.011 mmol, 17%) as a bright yellow solid. 1H NMR (500 MHz, CD3OD) δ 1.18-1.56 (m, 4H), 1.74-1.85 (m, 2H), 1.95-2.21 (m, 4H), 2.86-2.98 (m, 1H), 3.04 (s, 6H), 5.19 (d, J=16.1 Hz, 1H), 6.01 (d, J=16.1 Hz, 1H), 7.47 (d, J=2.2 Hz, 1H), 7.66 (dd, J=8.4, 1.5 Hz, 1H), 7.77-7.91 (m, 4H), 7.94 (d, J=1.8 Hz, 1H), 8.01 (d, J=8.4 Hz, 1H), 8.28 (s, 1H). LCMS: m/e 504 (M+H)+, ret time 1.81 min.

Workup

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

Sources & evidence

ORD record: ord-8a07064516ea48eba738fd56591fa9bb
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431568B2

Reaction notes

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