HCID 22598944, compound → HCID 60111028, compound

HRID 1007677Notes

Reaction equation

HRID 1007677 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[NH:7][CH2:8][CH2:9][CH2:10][N:11]1[C:19]2[C:14](=[CH:15][C:16]([C:20]([OH:22])=O)=[CH:17][CH:18]=2)[CH:13]=[N:12]1.[NH2:23][CH2:24][C@H:25]([NH:30][S:31]([C:34]1[CH:39]=[CH:38][C:37]([C:40]2[CH:45]=[CH:44][C:43]([S:46]([NH:49][CH2:50][CH2:51][NH:52][C:53]([O:55][CH2:56][C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)=[O:54])(=[O:48])=[O:47])=[CH:42][CH:41]=2)=[CH:36][CH:35]=1)(=[O:33])=[O:32])[C:26]([O:28][CH3:29])=[O:27]>>[C:57]1([CH2:56][O:55][C:53]([NH:52][CH2:51][CH2:50][NH:49][S:46]([C:43]2[CH:44]=[CH:45][C:40]([C:37]3[CH:38]=[CH:39][C:34]([S:31]([NH:30][C@@H:25]([CH2:24][NH:23][C:20]([C:16]4[CH:15]=[C:14]5[C:19](=[CH:18][CH:17]=4)[N:11]([CH2:10][CH2:9][CH2:8][NH:7][C:2]4[N:1]=[CH:6][CH:5]=[CH:4][N:3]=4)[N:12]=[CH:13]5)=[O:22])[C:26]([O:28][CH3:29])=[O:27])(=[O:32])=[O:33])=[CH:35][CH:36]=3)=[CH:41][CH:42]=2)(=[O:47])=[O:48])=[O:54])[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1

Participants

3

Reactant 2

HCID 22598944HCID 22598944, compoundHCID 57086315HCID 57086315, compound

Product 1

HCID 60111028HCID 60111028, compoundYield 60.1%

Procedure

The product of Example 40, Step B (58 mg, 195 umol) was reacted with the product of Example 44, Step A (144 mg, 205 umol) as in Example 44, Step B and the residue purified by preparative HPLC (Vydac C-18, 21.2 mm×25 cm, 90% acetonitrile/water/0.1% trifluoroacetic acid; 10-70% B over 30 minutes). The product fractions were combined, frozen, and lyophilized to afford the product as a white solid (102 mg, 54%). LRMS (ES): 870.3 ([M+H]+, 100%). 1HNMR (600.1343 MHz, DMSO-d6): 8.52 (d, 1H), 8.51 (s, 1H), 8.29 (d, 1H), 8.17, (d, 1H), 7.82 (m, 9H), 7.74 (d, 1H), 7.64 (d, 1H), 7.49 (b, 1H), 7.31, (m, 6H), 6.61 (t, 1H), 4.98, (s, 2H), 4.46 (t, 2H), 4.19 (dd, 1H), 3.55 (m, 1H), 3.42 (m, 1H), 3.41 (s, 3H), 3.26 (t, 2H), 3.06 (t, 2H), 2.83 (m, 2H), 2.09 (m, 2H).

Workup

  1. customthe residue purified by preparative HPLC (Vydac C-18, 21.2 mm×25 cm, 90% acetonitrile/water/0.1% trifluoroacetic acid; 10-70% B over 30 minutes)
  2. temperaturefrozen

Sources & evidence

ORD record
ord-50d707b6a17047b7acc8428854f76518
Source dataset
uspto-grants-2004_09
Patent number
US06794518B1

Reaction notes

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