1,2-Dichloroethane → HCID 10230850, compound

HRID 489655Notes

Reaction equation

HRID 489655 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].CCN(C(C)C)C(C)C.[NH:39]1[C:43](=[O:44])[CH2:42][CH2:41][CH:40]1[C:45](O)=[O:46].C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[Cl:29][C:26]1[CH:25]=[CH:24][C:23]([CH2:22][C@@H:2]([NH:1][C:45]([CH:40]2[CH2:41][CH2:42][C:43](=[O:44])[NH:39]2)=[O:46])[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

7

Reactant 5

HCID 111,2-DichloroethaneHCID 499Pyrrolidone carboxylic acidHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 69140350HCID 69140350, compound

Product 1

HCID 10230850HCID 10230850, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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) (118 mg, 0.25 mmol), DIEA (Aldrich) (0.05 mL, 0.25 mmol), DL-pyroglutamic acid (Aldrich) (344 mg, 0.5 mmol), HOAT (Aldrich) (68.2 mg, 0.5 mmol) and EDC (Aldrich) (95.8 mg, 0.5 mmol) in DMF (3 mL). Purification by silica gel chromatography (100% EtOAc) provided the title compound as a colorless film (82 mg). MS (ESI, pos. ion) m/z: 547 (M+1); (ESI, neg. ion) in/z: 545 (M−1). Calc'd for C26H31ClN4O5S: 546.17.

Workup

  1. customThe title compound was prepared
  2. customPurification by silica gel chromatography (100% EtOAc)

Sources & evidence

ORD record
ord-0a2647c431e14c35aff23e9193934af7
Source dataset
uspto-grants-2005_12
Patent number
US06977264B2

Reaction notes

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