Hydrochloric Acid → HCID 22144653, compound

HRID 1824980Notes

Reaction equation

HRID 1824980 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[CH2:6][C:7]([OH:9])=O.CN(C)CCCN=C=NCC.Cl.[NH2:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[N:28]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[F:39])[C:27]([C:40]([NH:42][C:43]1[CH:48]=[CH:47][C:46]([NH:49][C:50](=[O:56])[O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[CH:45][CH:44]=1)=[O:41])=[CH:26]2>CN(C)C1C=CN=CC=1.CN(C=O)C>[F:39][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=1[CH2:32][N:28]1[C:29]2[C:25](=[CH:24][C:23]([NH:22][C:7](=[O:9])[CH2:6][CH:2]3[CH2:3][CH2:4][CH2:5][O:1]3)=[CH:31][CH:30]=2)[CH:26]=[C:27]1[C:40]([NH:42][C:43]1[CH:44]=[CH:45][C:46]([NH:49][C:50](=[O:56])[O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[CH:47][CH:48]=1)=[O:41]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 2287262-(Oxolan-2-yl)acetic acidHCID 23573457HCID 23573457, compound

Product 1

HCID 22144653HCID 22144653, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

49 mg (0.38 mmol) of tetrahydro-2-furanylacetic acid, 19.3 mg (0.16 mmol) of 4-dimethylaminopyridine and 91 mg (0.47 mmol) of N′-(3-dimethylaminopropyl)-N-ethylcarbodiimide×HCl are added to 3 ml of DMF. 150 mg (0.32 mmol) of tert-butyl 4-({[5-amino-1-(2-fluorobenzyl)-1H-indol-2-yl]carbonyl}amino)phenyl-carbamate from Example XXIX are added. The mixture is stirred at RT for 5 hours. For work-up, the mixture is diluted and extracted with dichloromethane and aqueous hydrochloric acid. The organic phase is washed with sat. sodium bicarbonate solution, dried with sodium sulphate, filtered and concentrated under reduced pressure using a rotary evaporator. The residue is purified by preparative HPLC.

Workup

  1. additionFor work-up, the mixture is diluted
  2. extractionextracted with dichloromethane and aqueous hydrochloric acid
  3. washThe organic phase is washed with sat. sodium bicarbonate solution
  4. dry with materialdried with sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customa rotary evaporator
  8. customThe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-45c6fc02c8d445d1915396ed16b854a2
Source dataset
uspto-grants-2006_05
Patent number
US07045544B2

Reaction notes

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