1,2-Dichloroethane → HCID 69656109, compound

HRID 857787Notes

Reaction equation

HRID 857787 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:10]2[C:14]([Cl:15])=[N:13][S:12][N:11]=2)=[C:6]([CH2:8][NH2:9])[CH:7]=1.[C:16]([O:20][C:21]([NH:23][C@H:24]([CH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1)[C:25]([N:27]1[CH2:34][CH2:33][CH2:32][C@H:28]1[C:29](O)=[O:30])=[O:26])=[O:22])([CH3:19])([CH3:18])[CH3:17].C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[C:16]([O:20][C:21]([NH:23][C@H:24]([CH:35]1[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]1)[C:25]([N:27]1[CH2:34][CH2:33][CH2:32][C@H:28]1[C:29]([NH:9][CH2:8][C:6]1[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[C:10]1[C:14]([Cl:15])=[N:13][S:12][N:11]=1)=[O:30])=[O:26])=[O:22])([CH3:19])([CH3:17])[CH3:18]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 181649HOAtHCID 9975432(2R)-2-Cyclohexyl-N-[(1,1-dimethylethoxy)carbonyl]glycyl-L-prolineHCID 21866225HCID 21866225, compound

Product 1

HCID 69656109HCID 69656109, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 1-[5-chloro-2-(4-chloro-1,2,5-thiadiazol-3-yl)phenyl]methanamine (28.1 mg, 0.11 mmol), 1-{(2R)-2-[(tert-butoxycarbonyl)amino]-2-cyclohexylethanoyl}-L-proline (prepared by standard peptide coupling protocols, 38.3 mg, 0.11 mmol) and HOAt (19.1 mg, 0.14 mmol) in DMF (1.0 mL) was added EDC (26.9 g, 0.14 mmol). After 16 h the mixture was partitioned between EtOAc and water. The organic phase was washed with brine dried (Na2SO4) and reduced in vacuo. The residue was purified by HPLC (C18 eluting with an acetonitrile/water/0.1% TFA gradient). 1-{(2R)-2-[(tert-Butoxycarbonyl)amino]-2-cyclohexylethanoyl}-N-[5-chloro-2-(4-chloro-1,2,5-thiadiazol-3-yl)benzyl]-L-prolinamide was obtained as a solid. LCMS m/z=596.5.

Workup

  1. customAfter 16 h the mixture was partitioned between EtOAc and water
  2. washThe organic phase was washed with brine
  3. dry with materialdried (Na2SO4)
  4. customThe residue was purified by HPLC (C18
  5. washeluting with an acetonitrile/water/0.1% TFA gradient)

Sources & evidence

ORD record
ord-4ca4d32726054b61bd427dd2aeaae25c
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

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