1,2-Dichloroethane → HCID 86761386, compound

HRID 1669490Notes

Reaction equation

HRID 1669490 reaction equation
[NH2:1][S:2]([N:5]1[CH2:10][CH2:9][N:8]([CH2:11][CH2:12][CH2:13][CH:14]2[CH2:21][N:20]3[C:22]4[CH:23]=[C:24]([C:35](O)=[O:36])[CH:25]=[CH:26][C:27]=4[C:28]([CH:29]4[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]4)=[C:19]3[C:18]3[CH:38]=[CH:39][CH:40]=[CH:41][C:17]=3[O:16][CH2:15]2)[CH2:7][CH2:6]1)(=[O:4])=[O:3].C(Cl)CCl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH:29]1([C:28]2[C:27]3[CH:26]=[CH:25][C:24]4=[CH:23][C:22]=3[N:20]3[CH2:21][CH:14]([CH2:15][O:16][C:17]5[C:18]([C:19]=23)=[CH:38][CH:39]=[CH:40][CH:41]=5)[CH2:13][CH2:12][CH2:11][N:8]2[CH2:9][CH2:10][N:5]([CH2:6][CH2:7]2)[S:2](=[O:3])(=[O:4])[NH:1][C:35]4=[O:36])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

5

Reactant 2

HCID 111,2-DichloroethaneHCID 67344575HCID 67344575, compound

Product 1

HCID 86761386HCID 86761386, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 7-{3-[4-(aminosulfonyl)piperazin-1-yl]propyl}-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylic acid (0.04 M) in DCM were added EDC (1.5 eq) and DMAP (3 eq). The mixture was stirred at 50° C. for 2 h before cooling to RT and evaporating all volatiles in vacuo. The residue was purified by RP-HPLC (Waters Sunfire column; MeCN/H2O/0.1% TFA gradient). Fractions containing the pure compound were combined and lyophilized to afford the product as a white powder (19%). 1H NMR (400 MHz, DMSO-d6+TFA, 335 K) 1.16-1.23 (m, 2H), 1.31-1.39 (m, 2H), 1.47-1.50 (m, 1H), 1.69-1.73 (m, 2H), 1.83-2.19 (m, 7H), 2.64-2.66 (m, 1H), 3.29-3.36 (m, 4H), 3.49-3.74 (m, 7H), 3.89-3.93 (m, 2H), 4.28-4.39 (m, 1H), 4.40-4.44 (m, 1H), 7.28-7.32 (m, 2H), 7.35-7.37 (m, 1H), 7.45-7.47 (m, 1H), 7.52-7.56 (m, 1H), 7.90-7.92 (m, 2H); (ES+) m/z 563 (M+H)+.

Workup

  1. temperaturebefore cooling to RT
  2. customevaporating all volatiles in vacuo
  3. customThe residue was purified by RP-HPLC (Waters Sunfire column; MeCN/H2O/0.1% TFA gradient)
  4. additionFractions containing the pure compound

Sources & evidence

ORD record
ord-faed669d161748569df1b2a06fa74489
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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