HCID 178431478, compound → HCID 178508772, compound

HRID 2365509Notes

Reaction equation

HRID 2365509 reaction equation
CC1(C)[O:6][C@H:5]([CH2:7][O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[CH:15]=[C:14]([CH2:19][O:20][C:21]2[CH:50]=[CH:49][C:24]([C:25]([N:27]4[CH2:48][CH2:47][C:30]5([NH:34]/[C:33](=[N:35]/[C:36]([C:38]6[C:43]([NH2:44])=[N:42][C:41]([NH2:45])=[C:40]([Cl:46])[N:39]=6)=[O:37])/[NH:32][CH2:31]5)[CH2:29][CH2:28]4)=[O:26])=[CH:23][CH:22]=2)[CH:13]=[CH:12]3)[CH2:4][O:3]1>CO>[OH:6][C@@H:5]([CH2:4][OH:3])[CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([CH2:19][O:20][C:21]1[CH:50]=[CH:49][C:24]([C:25]([N:27]3[CH2:28][CH2:29][C:30]4([NH:34]/[C:33](=[N:35]/[C:36]([C:38]5[C:43]([NH2:44])=[N:42][C:41]([NH2:45])=[C:40]([Cl:46])[N:39]=5)=[O:37])/[NH:32][CH2:31]4)[CH2:47][CH2:48]3)=[O:26])=[CH:23][CH:22]=1)[CH:13]=[CH:12]2

Participants

3

Reactant 1

HCID 178431478HCID 178431478, compound

Product 1

HCID 178508772HCID 178508772, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3,5-diamino-6-chloro-pyrazine-2-carboxylic acid [8-{4-[6-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-naphthalen-2-ylmethoxy]-benzoyl}-1,3,8-triaza-spiro[4.5]dec-(2E)-ylidene]-amide (0.16 g, 0.22 mmol) in MeOH (10 ml) is added SCX-2 resin (˜2 g), the resultant slurry is stirred for 0.5 hours and then the solvent is removed in vacuo. The slurry is loaded onto a column of SCX-2 resin (˜3 g) and eluted with MeOH and then with 2 M NH3 in MeOH. The methanolic ammonia fractions are concentrated in vacuo and the residue is triturated with diethyl ether to obtain 3,5-Diamino-6-chloro-pyrazine-2-carboxylic acid [8-{-4-[6-((S)-2,3-dihydroxy-propoxy)-naphthalen-2-ylmethoxy]-benzoyl}-1,3,8-triaza-spiro[4.5]dec-(2E)-ylidene]-amide as yellow solid; [M+H]+ 675

Workup

  1. customthe solvent is removed in vacuo
  2. washeluted with MeOH
  3. concentrationThe methanolic ammonia fractions are concentrated in vacuo
  4. customthe residue is triturated with diethyl ether

Sources & evidence

ORD record
ord-b46478a795284dc881388bd7927b25d0
Source dataset
uspto-grants-2014_04
Patent number
US08697687B2

Reaction notes

Loading…