Methyl DL-serinate → N-cyclohexyl-N-methyl-4-(2-oxo-3-hydroxymethyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-7-yl)oxybutanamide

HRID 651998Notes

Reaction equation

HRID 651998 reaction equation
[CH:1]1([N:7]([CH2:26]COC(=O)C)[C:8](=[O:25])[CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[C:15]([C:22](=O)C)[CH:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[O:33][C:34](=O)[C@H:35]([CH2:37][OH:38])[NH2:36].COC(=O)[CH:43](CO)[NH2:44]>>[CH:1]1([N:7]([CH3:26])[C:8](=[O:25])[CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[C:15]3[C:16](=[CH:17][CH:18]=2)[N:19]=[C:43]2[NH:44][C:34](=[O:33])[CH:35]([CH2:37][OH:38])[N:36]2[CH2:22]3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 3

HCID 416960Methyl DL-serinateHCID 2723731(S)-methyl 2-amino-3-hydroxypropanoateHCID 20198535N-cyclohexyl-N-(2-acetoxyethyl)-4-(4-nitro-3-(1-oxoeth-1-yl)phenyl)oxybutanamide

Product 1

HCID 135626245N-cyclohexyl-N-methyl-4-(2-oxo-3-hydroxymethyl-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolin-7-yl)oxybutanamide

Procedure

Proceeding in a like manner but substituting the appropriate aldehyde of formula (6) as prepared in Preparation 4, or the appropriate ketone of formula (8) as prepared in either Preparation 6 or 9, and either L-serine methyl ester or a racemic mixture of D,L-serine methyl ester or similar ester, there are prepared the following exemplary compounds:

Workup

  1. customas prepared in Preparation 4
  2. customare prepared the following exemplary compounds

Sources & evidence

ORD record
ord-4820e9f66bda4ce3a21677e825ebff7d
Source dataset
uspto-grants-1987_06
Patent number
US04670434

Reaction notes

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