Ammonium Chloride → HCID 178513682, compound

HRID 1819435Notes

Reaction equation

HRID 1819435 reaction equation
[N+:1]([C:4]1[C:5]([NH:23][CH2:24][C@H:25]2[CH2:30][CH2:29][C@H:28]([N:31]3[CH2:34][CH2:33][CH:32]3[C:35](O)=[O:36])[CH2:27][CH2:26]2)=[N:6][C:7]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][C:19]([F:22])([F:21])[F:20])=[N:8][CH:9]=1)([O-:3])=[O:2].[Cl-].[NH4+].C[N:41](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[N+:1]([C:4]1[C:5]([NH:23][CH2:24][C@H:25]2[CH2:26][CH2:27][C@H:28]([N:31]3[CH2:34][CH2:33][CH:32]3[C:35]([NH2:41])=[O:36])[CH2:29][CH2:30]2)=[N:6][C:7]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][C:19]([F:20])([F:21])[F:22])=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178524544HCID 178524544, compound

Product 1

HCID 178513682HCID 178513682, compoundYield 5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(trans-4-{[(5-nitro-2-{[2-(trifluoromethoxy)benzyl]amino}pyrimidin-4-yl)amino]methyl}cyclohexyl)azetidine-2-carboxylic acid (170 mg, 0.27 mmol) in DMF (1.5 mL) were added ammonium chloride (170 mg, 3.2 mmol), HATU (303 mg, 0.80 mmol) and DIPEA (370 μL, 2.1 mmol). The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with EtOAc and washed with saturated NaHCO3, water (×3) and brine. The organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel preparative TLC using 95:5 CH2Cl2:MeOH as an eluent to afford 7 mg of the title compound, m/z 522.6 [M−1]+

Workup

  1. washwashed with saturated NaHCO3, water (×3) and brine
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe resulting residue was purified by silica gel preparative TLC

Sources & evidence

ORD record
ord-69ab8959a8194d918c1654c0718af98d
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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