1,2-Dichloroethane → HCID 59003071, compound

HRID 254011Notes

Reaction equation

HRID 254011 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([C:14]2[C:15]([NH2:27])=[N:16][CH:17]=[C:18]([C:20]3=[CH:21][CH2:22][NH:23][CH2:24][CH2:25][CH2:26]3)[CH:19]=2)=[N:12][N:11]=[N:10]1.C(Cl)CCl.[F:32][C:33]([F:38])([F:37])[C:34](O)=[O:35].CCN(C(C)C)C(C)C>C(Cl)Cl>[NH2:27][C:15]1[N:16]=[CH:17][C:18]([C:20]2[CH2:26][CH2:25][CH2:24][N:23]([C:34](=[O:35])[C:33]([F:38])([F:37])[F:32])[CH2:22][CH:21]=2)=[CH:19][C:14]=1[C:13]1[N:9]([C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=2[F:1])[N:10]=[N:11][N:12]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 66867193HCID 66867193, compound

Product 1

HCID 59003071HCID 59003071, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(1-(2,3-Difluorophenyl)-1H-tetrazol-5-yl)-5-((E)-2,5,6,7-tetrahydro-1H-azepin-4-yl)pyridin-2-amine (37 mg, 100 μmol, 1 eq.) was diluted in DCM (1.5 mL). EDC (34.4 mg, 150 μmol, 1.5 eq.), trifluoroacetic acid (17.1 mg, 150 μmol, 1 eq.), and DIEA (53 μL, 300 μmol, 3 eq.) were added. The reaction was stirred at room temperature overnight then concentrated. The product was purified by reversed-phase HPLC purification to give 1-((E)-5-(6-amino-5-(1-(2,3-difluorophenyl)-1H-tetrazol-5-yl)pyridin-3-yl)-3,4-dihydro-2H-azepin-1(7H)-yl)-2,2,2-trifluoroethanone (13.6 mg, 30% yield); 1H NMR (300 MHz, DMSO-d6): 8.25 (m, 1H); 7.87 (m, 1H); 7.77 (m, 1H); 7.55 (m, 1H); 7.37 (m, 1H); 5.95-5.7 (m, 1H); 4.12 (m, 2H); 3.75-3.6 (m, 2H); 2.4 (m, 2H); 1.75 (m, 2H).

Workup

  1. concentrationthen concentrated
  2. customThe product was purified by reversed-phase HPLC purification

Sources & evidence

ORD record
ord-38cc1a0b48804ec9aec3805d8ba503ab
Source dataset
uspto-grants-2011_01
Patent number
US07872031B2

Reaction notes

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