N,N-Dimethylsulfamide → (+/-)-13-Cyclohexyl-N-[(dimethylamino)sulfonyl]-6,7-dihydro-6-hydroxy-5H-indolo[2,1-a][2]benzazepine-10-carboxamide

HRID 1394881Notes

Reaction equation

HRID 1394881 reaction equation
Cl.CN(C)CCCN=C=NCC.[CH:13]1([C:19]2[C:20]3[CH:21]=[CH:22][C:23]([C:38](O)=[O:39])=[CH:24][C:25]=3[N:26]3[CH2:32][CH:31]([OH:33])[CH2:30][C:29]4[CH:34]=[CH:35][CH:36]=[CH:37][C:28]=4[C:27]=23)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[CH3:41][N:42]([CH3:47])[S:43]([NH2:46])(=[O:45])=[O:44]>CN(C1C=CN=CC=1)C.CN(C=O)C.C(Cl)Cl>[CH:13]1([C:19]2[C:20]3[CH:21]=[CH:22][C:23]([C:38]([NH:46][S:43]([N:42]([CH3:47])[CH3:41])(=[O:45])=[O:44])=[O:39])=[CH:24][C:25]=3[N:26]3[CH2:32][CH:31]([OH:33])[CH2:30][C:29]4[CH:34]=[CH:35][CH:36]=[CH:37][C:28]=4[C:27]=23)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1

Participants

7

Reactant 3

HCID 134472N,N-DimethylsulfamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58765272(+/-)13-cyclohexyl-6,7-dihydro-6-hydroxy-5H-indolo[2,1-a][2]benzazepine-10-carboxylic acid

Product 1

HCID 58765280(+/-)-13-Cyclohexyl-N-[(dimethylamino)sulfonyl]-6,7-dihydro-6-hydroxy-5H-indolo[2,1-a][2]benzazepine-10-carboxamide

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
22 °C

Procedure

1-[3-(Dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (11.5 mg, 0.06 mmol) was added to a solution of (±)13-cyclohexyl-6,7-dihydro-6-hydroxy-5H-indolo[2,1-a][2]benzazepine-10-carboxylic acid (7.5 mg, 0.02 mmol) and DMAP (7.4 mg, 0.06 mmol) in DMF (0.5 mL) and CH2Cl2 (0.5 mL) at 22° C. The vial was shaken for a minute at 22° C. N,N-Dimethylsulfamide (4.9 mg, 0.04 mmol) was then added. Stirring was continued for 18 hr. The solution was filtered and purified on the Shimadzu preparative liquid chromatograph. The product containing fraction was concentrated on a Speed Vac® to leave the titled compound as a white film (3.0 mg, 30%). ESI-MS m/z 482 (MH+); 1H NMR (500 MHz, MeOD) δ 1.26-1.34 (m, 1 H) 1.40-1.55 (m, 2 H) 1.63 (m, 1 H) 1.82 (m, 2 H) 1.96 (m, 1 H) 2.01-2.19 (m, 3 H) 2.36 (m, 1 H) 2.95-3.08 (m, 2 H) 3.03 (s, 6 H) 3.76 (dd, J=15.26, 3.36 Hz, 1H) 4.41-4.69 (m, 2 H) 7.40-7.50 (m, 4 H) 7.60 (m, 1 H) 7.93 (m, 1 H) 8.11 (m, 1 H).

Workup

  1. stirringStirring
  2. filtrationThe solution was filtered
  3. custompurified on the Shimadzu preparative liquid chromatograph
  4. additionThe product containing fraction
  5. concentrationwas concentrated on a Speed Vac®

Sources & evidence

ORD record
ord-6628d5711c3a456cbaee0f5b06872d08
Source dataset
uspto-grants-2008_03
Patent number
US07348425B2

Reaction notes

Loading…