Pyridine → HCID 57500372, compound

HRID 2273541Notes

Reaction equation

HRID 2273541 reaction equation
N1C=CC=CC=1.[C:7]([O:11][C:12](=[O:36])[NH:13][CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([NH:25][C:26]2[C:27]([CH3:35])=[CH:28][N:29]3[C:34]=2[CH:33]=[CH:32][CH:31]=[CH:30]3)=[O:24])[CH:18]=1)([CH3:10])([CH3:9])[CH3:8].Cl[C:38]([C:40]1[CH:41]=[CH:42][C:43]([NH:56][C:57](=[O:62])[C:58]([F:61])([F:60])[F:59])=[C:44]([CH:55]=1)[C:45]([O:47][CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)=[O:46])=[O:39]>ClCCl>[C:7]([O:11][C:12]([NH:13][CH2:14][CH2:15][O:16][C:17]1[CH:18]=[C:19]([CH:20]=[CH:21][CH:22]=1)[C:23]([NH:25][C:26]1[C:27]([CH3:35])=[C:28]([C:38]([C:40]2[CH:41]=[CH:42][C:43]([NH:56][C:57](=[O:62])[C:58]([F:61])([F:59])[F:60])=[C:44]([CH:55]=2)[C:45]([O:47][CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)=[O:46])=[O:39])[N:29]2[C:34]=1[CH:33]=[CH:32][CH:31]=[CH:30]2)=[O:24])=[O:36])([CH3:10])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 1049PyridineHCID 57500373HCID 57500373, compoundHCID 131733386HCID 131733386, compound

Product 1

HCID 57500372HCID 57500372, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.43 ml (43.7 mmol) of pyridine and 8.95 g (21.9 mmol) of tert-butyl[2-(3-{[(2-methylindolizin-1-yl)amino]-carbonyl}phenoxy)ethyl]carbamate are added to the suspension of 9.27 g (24.0 mmol) of benzyl 5-(chlorocarbonyl)-2-[(trifluoroacetyl)amino]benzoate in 180 ml of dichloromethane. The reaction medium that has turned greenish is stirred at ambient temperature for 16 hours. It is concentrated to dryness and the residue is taken up in diisopropyl ether and ethanol. The solid in suspension is filtered, washed with diisopropyl ether and dried. 6.29 g (38%) of a yellow powder are obtained.

Workup

  1. concentrationIt is concentrated to dryness
  2. filtrationThe solid in suspension is filtered
  3. washwashed with diisopropyl ether
  4. customdried

Sources & evidence

ORD record
ord-00e37e7f44c94954b5dd36ebff422c9f
Source dataset
uspto-grants-2015_09
Patent number
US09120819B2

Reaction notes

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