HCID 178431478, compound → HCID 178508772, compound

HRID 2281583Notes

Reaction equation

HRID 2281583 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-edcb7dbf25214eb598235b36f6b96509
Source dataset
uspto-grants-2015_09
Patent number
US09139586B2

Reaction notes

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