Ammonium Hydroxide → HCID 71269295, compound

HRID 1429387Notes

Reaction equation

HRID 1429387 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[S:11]([N:14]2[CH2:21][C:20]3[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=3[CH2:18][O:17][CH2:16][C@H:15]2[CH2:26][C:27](O)=[O:28])(=[O:13])=[O:12])[CH:4]=[CH:3][CH:2]=1.C[N:31](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[OH-].[NH4+]>C(Cl)Cl>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[S:11]([N:14]2[CH2:21][C:20]3[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=3[CH2:18][O:17][CH2:16][C@H:15]2[CH2:26][C:27]([NH2:31])=[O:28])(=[O:13])=[O:12])[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 14923Ammonium HydroxideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 71269312HCID 71269312, compound

Product 1

HCID 71269295HCID 71269295, compoundYield 32.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of compound 21a (100 mg, 0.24 mmol), HATU (137 mg, 0.36 mmol), DIPEA (77 mg, 0.6 mmol) in DCM (5 mL) was stirred at it for 0.5 hr. Ammonium hydroxide (12 mg, 0.36 mmol) was added and the mixture was stirred at it for 2 hr. The reaction mixture was quenched with water and extracted with DCM. The organic extracts were dried over anhydrous Na2SO4, filtered and concentrated. The crude product was purified by Prep-TLC to give the desired compound 23 (32 mg, 32% yield). LCMS (m/z): 412.2 (MH+).

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with DCM
  3. dry with materialThe organic extracts were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by Prep-TLC

Sources & evidence

ORD record
ord-4f705684cd0f451ba46a29306b748f45
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

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