Morpholine → HCID 178493888, compound

HRID 339784Notes

Reaction equation

HRID 339784 reaction equation
CS(OC[C@H]1OC1)(=O)=O.[CH3:10][O:11][C:12]1[C:21]2[N:20]=[C:19]([NH2:22])[N:18]3[CH2:23][CH2:24][N:25]=[C:17]3[C:16]=2[CH:15]=[CH:14][C:13]=1[O:26][CH2:27][C@H:28]1[CH2:30][O:29]1.[NH:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1.[CH3:37][C:38]1[C:43]([C:44](O)=[O:45])=[CH:42][CH:41]=[CH:40][N:39]=1>CO.C(Cl)Cl.CO>[OH:29][C@@H:28]([CH2:30][N:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1)[CH2:27][O:26][C:13]1[CH:14]=[CH:15][C:16]2[C:17]3[N:18]([CH2:23][CH2:24][N:25]=3)[C:19]([NH:22][C:44]([C:43]3[C:38]([CH3:37])=[N:39][CH:40]=[CH:41][CH:42]=3)=[O:45])=[N:20][C:21]=2[C:12]=1[O:11][CH3:10]

Participants

7

Reactant 4

HCID 8083MorpholineHCID 6433732-Methylnicotinic acidHCID 12461090(S)-glycidyl methanesulfonate2×HCID 178493879HCID 178493879, compound

Product 1

HCID 178493888HCID 178493888, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared using (S)-glycidyl methanesulfonate (Intermediate H, Step 1) in place of (R)-glycidyl methanesulfonate (Intermediate F, Step 1), and morpholine in place of piperidine in Step 1, and 2-methyl-3-pyridinecarboxylic acid in place of nicotinic acid in Step 2 (0.059 g, 56%): TLC (9:1 CH2Cl2/MeOH+1% NH4OH in MeOH)Rf 0.44; HPLC ret. time 0.81 min.; 1H NMR (DMSO-d6+1 drop TFA-d) δ 2.99 (s, 3H), 3.09-3.40 (m, 4H), 3.48 (br d, J=12.1 Hz, 2H), 3.63-3.83 (m, 2H), 3.89-4.01 (m, 2H), 4.02 (s, 3H), 4.18-4.29 (m, 4H), 4.38-4.46 (m, 1H), 4.46-4.55 (m, 2H), 7.50 (d, J=9.0 Hz, 1H), 7.96 (dd, J=6.2, 7.5 Hz, 1H), 8.05 (d, J=9.0 Hz, 1H), 8.91 (d, J=5.5 Hz, 1H), 9.06 (br d, J=8.3 Hz, 1H); mass spectrum m/z 495 ((M+1)+, 2.3%).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-68442aeb13d748458fb44612f4570eb0
Source dataset
uspto-grants-2014_11
Patent number
US08895549B2

Reaction notes

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