HCID 10513510, compound → HCID 70153539, compound

HRID 1017193Notes

Reaction equation

C(O[C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17](OCC2C=CC=CC=2)=O)[CH2:13][C@@H:12]1[C:27](O)=O)=O)C1C=CC=CC=1.[Cl:30][C:31]1[CH:32]=[CH:33][CH:34]=[C:35]2[C:39]=1[NH:38][C:37]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[CH:36]2>>[ClH:30].[ClH:30].[Cl:30][C:31]1[CH:32]=[CH:33][CH:34]=[C:35]2[C:39]=1[NH:38][C:37]([C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)=[C:36]2[CH2:27][C@H:12]1[CH2:13][N:14]([CH3:17])[CH2:15][CH2:16][N:11]1[CH3:9]

Participants

Reactant 2

HCID 10513510HCID 10513510, compound

HCID 70152758HCID 70152758, compound

Product 1

HCID 70153539HCID 70153539, compound

Procedure

By substantially following the procedures of Example 1, utilising di-N-benzyloxycarbonylpiperazine-2(R)-carboxylic acid in place of N-benzyloxycarbonylnipecotic acid and 7-chloro-2-phenylindole in place of 2-phenylindole, was prepared the title compound as a white solid. (Found: C, 57.69; H, 6.11; N, 9.56; C21H24Cl3N2.0.6H2O requires C, 57.64; H, 6.27; N, 9.60%); mp 260° C. (from EtOH); [α]D22+25.2 (c 1.0 in MeOH); δH (400 MHz; D2O) 2.38 (4H, m, CH3 and aliphatic), 2.58 (3H, s, CH3), 2.70-2.88 (5H, m, aliphatics), 3.16-3.21 (2H, m, aliphatics), 3.50 (1H, m, aliphatic), 7.19 (1H, t, J 7.9 and 7.8, indole H5), 7.32 (1H, dd, J 7.6 and 0.6, indole H6), 7.51-7.55 (1H, m, aromatic), 7.57-7.63 (8H, m, aromatics); m/z (ES30) 353 (M++H, 100%).

Sources & evidence

ORD record: ord-5a0f54a051074722a6b2447b75159e27
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06479480B1

Reaction notes

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