1,2-Dichloroethane → Ethyl 5-(13-cyclohexyl-10-((isopropylsulfonyl)carbamoyl)-3-methoxy-7H-indolo[2,1-a][2]benzazepin-6-yl)-1-cyclopropyl-3-isopropyl-1H-pyrazole-4-carboxylate

HRID 1094542Notes

Reaction equation

HRID 1094542 reaction equation
C(Cl)CCl.[CH:5]1([C:11]2[C:12]3[CH:13]=[CH:14][C:15]([C:47]([OH:49])=O)=[CH:16][C:17]=3[N:18]3[CH2:24][C:23]([C:25]4[N:29]([CH:30]5[CH2:32][CH2:31]5)[N:28]=[C:27]([CH:33]([CH3:35])[CH3:34])[C:26]=4[C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:22][C:21]4[CH:41]=[C:42]([O:45][CH3:46])[CH:43]=[CH:44][C:20]=4[C:19]=23)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[CH3:50][CH:51]([S:53]([NH2:56])(=[O:55])=[O:54])[CH3:52]>CN(C1C=CN=CC=1)C.ClC(Cl)C.CCOC(C)=O>[CH:5]1([C:11]2[C:12]3[CH:13]=[CH:14][C:15]([C:47](=[O:49])[NH:56][S:53]([CH:51]([CH3:52])[CH3:50])(=[O:55])=[O:54])=[CH:16][C:17]=3[N:18]3[CH2:24][C:23]([C:25]4[N:29]([CH:30]5[CH2:31][CH2:32]5)[N:28]=[C:27]([CH:33]([CH3:35])[CH3:34])[C:26]=4[C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:22][C:21]4[CH:41]=[C:42]([O:45][CH3:46])[CH:43]=[CH:44][C:20]=4[C:19]=23)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

7

Reactant 3

HCID 111,2-DichloroethaneHCID 3549191Propane-2-sulfonamideHCID 5795385013-cyclohexyl-6-(1-cyclopropyl-4-(ethoxycarbonyl)-3-isopropyl-1H-pyrazol-5-yl)-3-methoxy-7H-indolo[2,1-a][2]benzazepine-10-carboxylic Acid

Product 1

HCID 57953778Ethyl 5-(13-cyclohexyl-10-((isopropylsulfonyl)carbamoyl)-3-methoxy-7H-indolo[2,1-a][2]benzazepin-6-yl)-1-cyclopropyl-3-isopropyl-1H-pyrazole-4-carboxylateYield 99.8%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 63651,1-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

EDC (151 mg, 0.790 mmol) was added to a stirring solution of 13-cyclohexyl-6-(1-cyclopropyl-4-(ethoxycarbonyl)-3-isopropyl-1H-pyrazol-5-yl)-3-methoxy-7H-indolo[2,1-a][2]benzazepine-10-carboxylic acid (320 mg, 0.527 mmol), propane-2-sulfonamide (227 mg, 1.843 mmol), DMAP (193 mg, 1.58 mmol) in dichloroethane (5 mL) at room temperature. The reaction was allowed to stir overnight. The mixture was diluted with EtOAc and washed with 1M HCl, sat NaHCO3 and Brine. The organic phase was dried over Na2SO4, filtered and concentrated to give the expected product (375 mg, 0.526 mmol, quant) as a light brown residue consistent by LCMS.

Workup

  1. washwashed with 1M HCl
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6b01eeb495584f68a937911b6d82167e
Source dataset
uspto-grants-2012_03
Patent number
US08133884B2

Reaction notes

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