1,2-Dichloroethane → HCID 89533518, compound

HRID 1466181Notes

Reaction equation

HRID 1466181 reaction equation
[O:1]=[C:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[CH:8]1[CH2:17][CH2:16][C:15]2[CH:14]=[C:13]([C:18]#[N:19])[CH:12]=[CH:11][C:10]=2[CH2:9]1.[N:20]1([C:25]2[CH:26]=[C:27]3[C:31](=[CH:32][CH:33]=2)[CH:30]([C:34](O)=[O:35])[CH2:29][CH2:28]3)[CH:24]=[N:23][N:22]=[N:21]1.C(Cl)CCl>CN(C1C=CN=CC=1)C.ClC(Cl)C>[O:1]=[C:2]1[CH2:7][N:6]([C:34]([CH:30]2[C:31]3[C:27](=[CH:26][C:25]([N:20]4[CH:24]=[N:23][N:22]=[N:21]4)=[CH:33][CH:32]=3)[CH2:28][CH2:29]2)=[O:35])[CH2:5][CH2:4][N:3]1[CH:8]1[CH2:17][CH2:16][C:15]2[CH:14]=[C:13]([C:18]#[N:19])[CH:12]=[CH:11][C:10]=2[CH2:9]1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 67517270HCID 67517270, compoundHCID 895249666-(2-Oxopiperazin-1-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

Product 1

HCID 89533518HCID 89533518, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 63651,1-DichloroethaneSolvent

Procedure

A mixture of 6-(2-Oxopiperazin-1-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile (40 mg, 0.16 mmol) (20 mg, 0.078 mmol), 5-(1H-tetrazol-1-yl)-2,3-dihydro-1H-indene-1-carboxylic acid (18 mg, 0.078 mmol), DMAP (14 mg, 0.12 mmol), and EDC (23 mg, 0.12 mmol) was stirred in dichloroethane (2 mL) for 2 hours. The solvent was removed under vacuum, and the residue was redissolved in methanol, and purified by reverse phase HPLC to give the title product. LC-MS (IE, m/z): 468 [M+1]+.

Workup

  1. customThe solvent was removed under vacuum
  2. dissolutionthe residue was redissolved in methanol
  3. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-4c6f1214c68d417fa02e326eae0eb0eb
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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