Water → HCID 87289434, compound

HRID 476220Notes

Reaction equation

HRID 476220 reaction equation
[CH2:1]([CH:3]1[CH:20]([OH:21])[CH:19]([CH3:22])[CH:18]=[C:17]([CH3:23])[CH:16]=[C:15]([O:24][CH3:25])[C:14](=[O:26])[O:13][CH:12]([CH:27]([CH:29]([OH:48])[CH:30]([CH3:47])/[C:31](=[N:41]\[O:42][CH2:43][C:44](O)=[O:45])/[CH:32]=[CH:33]/[CH:34]([CH3:40])[CH:35]([OH:39])/[CH:36]=[CH:37]/[CH3:38])[CH3:28])[CH:11]([O:49][CH3:50])[CH:10]=[CH:9][CH:8]=[C:7]([CH3:51])[CH2:6][CH:5]([CH3:52])[CH:4]1[OH:53])[CH3:2].C1C=CC2N(O)N=NC=2C=1.[N:64]1([CH:70]2[CH2:75][CH2:74][NH:73][CH2:72][CH2:71]2)[CH2:69][CH2:68][CH2:67][CH2:66][CH2:65]1.O>ClCCl>[N:64]1([CH:70]2[CH2:75][CH2:74][N:73]([C:44](=[O:45])[CH2:43][O:42]/[N:41]=[C:31](/[CH:32]=[CH:33]/[CH:34]([CH3:40])[CH:35]([OH:39])/[CH:36]=[CH:37]/[CH3:38])\[CH:30]([CH3:47])[CH:29]([OH:48])[CH:27]([CH:12]3[O:13][C:14](=[O:26])[C:15]([O:24][CH3:25])=[CH:16][C:17]([CH3:23])=[CH:18][CH:19]([CH3:22])[CH:20]([OH:21])[CH:3]([CH2:1][CH3:2])[CH:4]([OH:53])[CH:5]([CH3:52])[CH2:6][C:7]([CH3:51])=[CH:8][CH:9]=[CH:10][CH:11]3[O:49][CH3:50])[CH3:28])[CH2:72][CH2:71]2)[CH2:69][CH2:68][CH2:67][CH2:66][CH2:65]1

Participants

6

Reactant 4

HCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 786071,4'-BipiperidineHCID 88876342HCID 88876342, compound

Product 1

HCID 87289434HCID 87289434, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound of example 10 (10 mg) in dichloromethane (2 mL) dicyclohexylcarbodiimide (3 mg), and HOBT (2 mg) were added. After 20 min, 4-piperidino-piperidine 2.5 mg) was added. The reaction mixture was stirred for 18 h under nitrogen atmosphere. Cold water was added to the reaction mixture, the organic layer was separated; Reaction mixture was extracted with dichloromethane (3×5 mL). The combined organic layer was washed with water (2×5 mL). The organic layer was dried over sodium sulphate, and was concentrated. The crude product was purified by preparative HPLC [Eurospere-100, C18 column (250 mm×8 mm), mobile phase: acetonitrile-water (1:1 isocratic)] to obtain the title compound.

Workup

  1. customthe organic layer was separated
  2. customReaction mixture
  3. extractionwas extracted with dichloromethane (3×5 mL)
  4. washThe combined organic layer was washed with water (2×5 mL)
  5. dry with materialThe organic layer was dried over sodium sulphate
  6. concentrationwas concentrated
  7. customThe crude product was purified by preparative HPLC [Eurospere-100, C18 column (250 mm×8 mm), mobile phase: acetonitrile-water (1:1 isocratic)]

Sources & evidence

ORD record
ord-ed4e34f801704153ac39625b8d02a83b
Source dataset
uspto-grants-2014_01
Patent number
US08637683B2

Reaction notes

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