HCID 68667072, compound → HCID 67226250, compound

HRID 1848851Notes

Reaction equation

HRID 1848851 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][C:12]([CH3:15])([CH3:14])[CH2:11][CH2:10][C:9]=2[CH2:16][N:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:51]=[CH:50][C:26]([C:27]([NH:29][S:30]([C:33]4[CH:38]=[CH:37][C:36]([NH:39][CH:40]5[CH2:45][CH2:44][N:43]([CH3:46])[CH2:42][CH2:41]5)=[C:35]([N+:47]([O-:49])=[O:48])[CH:34]=4)(=[O:32])=[O:31])=[O:28])=[C:25]([O:52][C:53]4[CH:58]=[CH:57][CH:56]=[C:55]([O:59]COC)[CH:54]=4)[CH:24]=3)[CH2:19][CH2:18]2)=[CH:4][CH:3]=1>O1CCCC1.Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][C:12]([CH3:15])([CH3:14])[CH2:11][CH2:10][C:9]=2[CH2:16][N:17]2[CH2:18][CH2:19][N:20]([C:23]3[CH:51]=[CH:50][C:26]([C:27]([NH:29][S:30]([C:33]4[CH:38]=[CH:37][C:36]([NH:39][CH:40]5[CH2:45][CH2:44][N:43]([CH3:46])[CH2:42][CH2:41]5)=[C:35]([N+:47]([O-:49])=[O:48])[CH:34]=4)(=[O:32])=[O:31])=[O:28])=[C:25]([O:52][C:53]4[CH:58]=[CH:57][CH:56]=[C:55]([OH:59])[CH:54]=4)[CH:24]=3)[CH2:21][CH2:22]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 68667072HCID 68667072, compound

Product 1

HCID 67226250HCID 67226250, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of EXAMPLE 176E (35.5 mg) in tetrahydrofuran (3 mL) and HCl (1.25M in methanol, 2 mL) was stirred for 1 hour at 60° C. The product was concentrated. The crude product was purified by RP HPLC (C8, 30%-100% CH3CN/water/0.1% TFA) to yield the product. 1H NMR (300 MHz, dimethylsulfoxide-d6) δ 9.31 (s, 1H), 8.10 (s, 1H), 7.66-7.73 (m, 2H), 7.56 (d, 1H), 7.34-7.38 (m, 2H), 7.02-7.09 (m, 2H), 6.95-7.02 (m, 1H), 6.65 (dd, 1H), 6.34 (s, 1H), 6.29 (d, 1H), 6.20 (d, 1H), 6.14 (d, 1H), 4.14 (dd, 1H), 3.75 (s, 1H), 3.05 (d, 4H), 2.68-2.80 (m, 3H), 2.20 (d, 6H), 2.08 (d, 2H), 1.97 (s, 2H), 1.69-1.79 (m, 2H), 1.63 (s, 1H), 1.39 (d, 2H), 1.21-1.36 (m, 9H), 0.94 (s, 6H).

Workup

  1. concentrationThe product was concentrated
  2. customThe crude product was purified by RP HPLC (C8, 30%-100% CH3CN/water/0.1% TFA)
  3. customto yield the product

Sources & evidence

ORD record
ord-04b2591029df489e8915f25ab5636f65
Source dataset
uspto-grants-2015_02
Patent number
US08952157B2

Reaction notes

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