Morpholine → HCID 178493891, compound

HRID 339785Notes

Reaction equation

HRID 339785 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.[NH2:37][C:38]1[N:43]=[CH:42][C:41]([C:44](O)=[O:45])=[CH:40][N:39]=1>>[NH2:37][C:38]1[N:43]=[CH:42][C:41]([C:44]([NH:22][C:19]2[N:18]3[CH2:23][CH2:24][N:25]=[C:17]3[C:16]3[CH:15]=[CH:14][C:13]([O:26][CH2:27][C@@H:28]([OH:29])[CH2:30][N:31]4[CH2:36][CH2:35][O:34][CH2:33][CH2:32]4)=[C:12]([O:11][CH3:10])[C:21]=3[N:20]=2)=[O:45])=[CH:40][N:39]=1

Participants

5

Reactant 4

HCID 8083MorpholineHCID 70203672-aminopyrimidine-5-carboxylic AcidHCID 12461090(S)-glycidyl methanesulfonate2×HCID 178493879HCID 178493879, compound

Product 1

HCID 178493891HCID 178493891, compound

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-amino-5-pyrimidinecarboxylic acid in place of nicotinic acid in Step 2 (75.0 mg, 71%): HPLC ret. time 0.81 min.; 1H NMR (DMSO-d6+1 drop TFA-d) δ 3.14-3.38 (m, 4H), 3.44-3.52 (m, 2H), 3.69 (app t, J=12.0 Hz, 1H), 3.77/app t, J=12.1 Hz, 1H), 3.90-3.98 (m, 2H), 4.00 (s, 3H), 4.16-4.25 (m, 4H), 4.38-4.44 (m, 1H), 4.46-4.52 (m, 2H), 7.43 (d, J=9.1 Hz, 1H), 7.99 (d, J=9.1 Hz, 1H), 8.97 (s, 2H); mass spectrum m/z 497 ((M+1)+, 8.8%).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-93865345d3ad43658a2d7c7da1315eea
Source dataset
uspto-grants-2014_11
Patent number
US08895549B2

Reaction notes

Loading…