Toluene → HCID 178459641, compound

HRID 849422Notes

Reaction equation

HRID 849422 reaction equation
Cl.[C:2](N1CC2C=C(C3C=CC=CC=3)C=CC=2N(CC2N=CNC=2)C[C@H]1CC1C=CC=CC=1)(=O)C.[NH2:35][C:36]1[CH:66]=[CH:65][C:39]2[CH2:40][N:41]([C:58]([O:60][C:61]([CH3:64])([CH3:63])C)=[O:59])[CH:42]([CH2:51][C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[CH2:43][N:44]([CH2:45][C:46]3[N:47]=[CH:48][NH:49][CH:50]=3)[C:38]=2[CH:37]=1.C1(C)C=CC=CC=1.[Cl:74]C(OC(C)C)=O>CCOC(C)=O.CCCCCC>[ClH:74].[C:36]([C:66]1[CH:2]=[CH:37][C:38]2[N:44]([CH2:45][C:46]3[N:47]=[CH:48][NH:49][CH:50]=3)[CH2:43][C@@H:42]([CH2:51][C:52]3[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=3)[N:41]([C:58]([O:60][CH:61]([CH3:63])[CH3:64])=[O:59])[CH2:40][C:39]=2[CH:65]=1)#[N:35]

Participants

7

Reactant 4

HCID 1140TolueneHCID 7917Isopropyl chloroformateHCID 178451486HCID 178451486, compoundHCID 178473725HCID 178473725, compound

Product 1

HCID 178459641HCID 178459641, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Example 358 was prepared as a light yellow solid in 42% yield from Compound C of Example 248 by the following sequence: Compound E of Example 248, using a toluene solution of isopropyl chloroformate with chromatography using 40% hexane in EtOAc and with the free base carried on; Example 354. MS: [M+H]+ =430.

Sources & evidence

ORD record
ord-ae5ad0235d434d5a86b57399cb157de7
Source dataset
uspto-grants-2000_01
Patent number
US06011029

Reaction notes

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