Methyl chloroformate → HCID 131722407, compound

HRID 1355654Notes

Reaction equation

HRID 1355654 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18]([F:21])([F:20])[F:19])=[CH:15][CH:16]=2)[C@H:11]([NH2:22])[CH2:10][C@@H:9]1[CH:23]1[CH2:25][CH2:24]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:26][C:27]([F:41])([F:40])[C:28]1[CH:29]=[C:30]([CH:33]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:35]=1)[CH:31]=O.Cl[C:43]([O:45][CH3:46])=[O:44]>>[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18]([F:19])([F:21])[F:20])=[CH:15][CH:16]=2)[C@H:11]([N:22]([CH2:31][C:30]2[CH:29]=[C:28]([C:27]([F:41])([F:40])[F:26])[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:33]=2)[C:43]([O:45][CH3:46])=[O:44])[CH2:10][C@@H:9]1[CH:23]1[CH2:24][CH2:25]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 6586Methyl chloroformateHCID 1362473,5-Bis(trifluoromethyl)benzaldehydeHCID 69695297HCID 69695297, compound

Product 1

HCID 131722407HCID 131722407, compound

Procedure

cis-4-Amino-2-cyclopropyl-6-trifluoromethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester (Example 107C) (1.0 g) was subjected to reductive amination (with 3,5-bis(trifluoromethyl)benzaldehyde as in Example 4 and acylation with methyl chloroformate as in Example 5) to afford 2.4 g of the title compound. MS m/z 640 (M+); 1H NMR (CDCl3) δ 1.5 (s, 9H), 3.8 (s, 3H), 7.1 (s, 1H), 7.5-8.0 (m, 4H).

Sources & evidence

ORD record
ord-41be7de25bb04327bfd057132d458dda
Source dataset
uspto-grants-2003_07
Patent number
US06586448B1

Reaction notes

Loading…