Diisopropylethylamine → HCID 21060080, compound

HRID 228094Notes

Reaction equation

HRID 228094 reaction equation
ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.OC(C(F)(F)F)=O.[NH2:20][C@H:21]([CH2:41][C:42]1[CH:47]=[CH:46][C:45]([Cl:48])=[CH:44][CH:43]=1)[C:22]([N:24]1[CH2:29][CH2:28][N:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[NH:36][S:37]([CH3:40])(=[O:39])=[O:38])[CH2:26][CH2:25]1)=[O:23].CCN(C(C)C)C(C)C.C([O:62][C:63](=O)[NH:64][CH2:65][CH2:66][CH2:67][NH2:68])(C)(C)C>>[Cl:48][C:45]1[CH:44]=[CH:43][C:42]([CH2:41][C@@H:21]([NH:20][C:63]([NH:64][CH2:65][CH2:66][CH2:67][NH2:68])=[O:62])[C:22]([N:24]2[CH2:25][CH2:26][N:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[NH:36][S:37]([CH3:40])(=[O:38])=[O:39])[CH2:28][CH2:29]2)=[O:23])=[CH:47][CH:46]=1

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 86590295HCID 86590295, compound

Product 1

HCID 21060080HCID 21060080, compound

Procedure

Following the procedure of Example 51, N-[(1R)-1-[(4-chlorophenyl)methyl]-2-(4-{2-[(methylsulfonyl)amino]phenyl}piperazinyl)-2-oxoethyl][(3-aminopropyl)amino]carboxamide, TFA salt was prepared from triphosgene (Avocado Chemical Company) (45 mg, 0.152 mmol), (2R)-2-amino-3-(4-chlorophenyl)-1-(4-{2-[(methylsulfonyl)amino]phenyl}piperazinyl)propan-1-one TFA salt (200 mg, 0.36 mmol), DIEA (0.32 mL, 0.916 mmol), and tert-butyl-N-(3-aminopropyl)carbamate (Aldrich Chemical Company) (96 mg, 0.55 mmol). The Boc protecting group was removed by treating the compound with a soln of 50% TFA and CH2Cl2 (2 mL) for 2 h. The organic solvent was removed in vacuo to give the desired product. Preparative TLC purification with 60% Hexane, 35% CH2Cl2 and 5% 2N NH3 in MeOH afforded 90% pure compound. This was further purified by preparative HPLC (TFA buffer) to afford the title compound (TFA salt) as a white solid (10 mg). MS (ESI, pos. ion) m/z: 537 (M+H); MS (ESI, neg. ion) m/z: 535 (M−H). Calc'd for C24H33ClN6O4S: 536.20.

Workup

  1. customThe Boc protecting group was removed
  2. additionby treating the compound with a soln of 50% TFA and CH2Cl2 (2 mL) for 2 h
  3. customThe organic solvent was removed in vacuo

Sources & evidence

ORD record
ord-f786f1ca001d462db349f8cc73994f51
Source dataset
uspto-grants-2009_07
Patent number
US07560460B2

Reaction notes

Loading…