1,2-Dichloroethane → HCID 10187421, compound

HRID 489650Notes

Reaction equation

HRID 489650 reaction equation
[NH2:1][C@H:2]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)[C:3]([N:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH2:7][CH2:6]1)=[O:4].C1C=NC2N([OH:39])N=NC=2C=1.C(Cl)CCl.C[CH2:45][N:46]([CH:50]([CH3:52])[CH3:51])[CH:47]([CH3:49])C>>[Cl:29][C:26]1[CH:25]=[CH:24][C:23]([CH2:22][C@@H:2]([NH:1][C:52]([C@@H:50]2[CH2:51][CH2:49][CH2:47][N:46]2[CH3:45])=[O:39])[C:3]([N:5]2[CH2:10][CH2:9][CH:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[NH:17][S:18]([CH3:21])(=[O:19])=[O:20])[CH2:7][CH2:6]2)=[O:4])=[CH:28][CH:27]=1

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 69140350HCID 69140350, compound

Product 1

HCID 10187421HCID 10187421, compoundYield 45.7%

Procedure

The title compound was prepared according to the procedure described in Example 1, Step (f) using (2R)-2-amino-3-(4-chlorophenyl)-1-(4-{2-[(methylsulfonyl)-amino]phenyl}piperidyl)propan-1-one (Example 1, Step g) (210 mg, 0.48 mmol), N-methyl S-proline (Hachem Company) (68 mg, 0.53 mmol), HOAT (Aldrich) (65 mg, 0.48 mmol), EDC (Aldrich) (184 mg, 0.96 mmol) and DIEA (Aldrich) (84 μL, 0.48 mmol). Purification by reverse phase preparative HPLC (Phenomenex; 5 μm 250×21.2 mm, 5% to 95% CH3CN (0.1% TFA) in H2O (0.1% TFA) over 30 min, then 100% CH3CN (0.1% TFA) for 2 min]provided the title compound as a colorless oil (120 mg). MS (ESI, pos. ion) m/z: 547 (M+1). Calc'd for C27H35ClN4O4S: 546.21.

Workup

  1. customThe title compound was prepared
  2. customPurification by reverse phase preparative HPLC (Phenomenex

Sources & evidence

ORD record
ord-692ac5ef72394cbe963fc94114f13f34
Source dataset
uspto-grants-2005_12
Patent number
US06977264B2

Reaction notes

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