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Ammonium Chloride → HCID 178418829, compound

HRID 1181245
Notes
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Reaction equation

HRID 1181245 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([C:14]#[N:15])[CH:9]=2)[N:5]=[C:4]([NH:16][S:17](=[O:27])(=[O:26])[NH:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:3]=1[O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[O:35][CH3:36].[N-:37]=[N+:38]=[N-:39].[Na+].[Cl-].[NH4+]>CN(C=O)C>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([C:14]3[NH:39][N:38]=[N:37][N:15]=3)[CH:9]=2)[N:5]=[C:4]([NH:16][S:17](=[O:26])(=[O:27])[NH:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:3]=1[O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[O:35][CH3:36]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 21041243Benzylsulfamic acid [6-chloro-2-(2-cyano-pyridin-4-yl)-5-(2-methoxy-phenoxy) pyrimidin-4-yl]-amide

Product 1

HCID 178418829HCID 178418829, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6228Dimethylformamide
Solvent

Conditions

Temperature
80 °C

Procedure

Benzylsulfamic acid [6-chloro-2-(2-cyano-pyridin-4-yl)-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide (4.17 g) was dissolved in DMF (55 ml). Sodium azide (5.2 g) and ammonium chloride (4.28 g) were added and the mixture was stirred for 20 h at 80° C. Then the mixture was pored onto water and extracted with EtOAc. The layers were separated and the water layer was acidified with acetic acid to pH ˜5 and extracted with EtOAc. The combined organic layers from the 2nd extraction were washed with brine, dried over magnesium sulfate, filtered and evaporated. The crude material was purified by chromatography over silicagel with EtOAc/MeOH/ammonia=5/1/0.5 to give benzylsulfamic acid [6-chloro-5-(2-methoxy-phenoxy)-2-[2-(1H-tetrazol-5-yl)-pyridin-4-yl]-pyrimidin-4-yl]-amide (1.67 g). LC-MS: tR=5.02; [M+H]+=566.36.

Workup

  1. extractionextracted with EtOAc
  2. customThe layers were separated
  3. extractionextracted with EtOAc
  4. extractionThe combined organic layers from the 2nd extraction
  5. washwere washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude material was purified by chromatography over silicagel with EtOAc/MeOH/ammonia=5/1/0.5

Sources & evidence

ORD record
ord-e66f8dcedf64450eb4bf2f854c1c951a
Source dataset
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07285549B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes