Ammonia → 3-(2-Amino-2-oxoethyl)-N-{2,4-dimethyl-5-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]-phenyl}-5-(pentafluoro-lambda6-sulphanyl)benzamide

HRID 1055762Notes

Reaction equation

HRID 1055762 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N:9]2[C:16]3[N:12]([N:13]=[C:14]([C:17]4[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=4)[CH:15]=3)[CH:11]=[CH:10]2)=[CH:4][C:3]=1[NH:23][C:24]([C:26]1[CH:27]=[C:28]([CH2:38][C:39](O)=[O:40])[CH:29]=[C:30]([S:32]([F:37])([F:36])([F:35])([F:34])[F:33])[CH:31]=1)=[O:25].C[N:43](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.N.CCCCC.C(OC(C)C)(C)C>CN(C=O)C.C1COCC1>[NH2:43][C:39](=[O:40])[CH2:38][C:28]1[CH:27]=[C:26]([CH:31]=[C:30]([S:32]([F:36])([F:37])([F:34])([F:33])[F:35])[CH:29]=1)[C:24]([NH:23][C:3]1[CH:4]=[C:5]([N:9]2[C:16]3[N:12]([N:13]=[C:14]([C:17]4[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=4)[CH:15]=3)[CH:11]=[CH:10]2)[C:6]([CH3:8])=[CH:7][C:2]=1[CH3:1])=[O:25]

Participants

8

Reactant 5

HCID 222AmmoniaHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 71667103[3-({2,4-Dimethyl-5-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}carbamoyl)-5-(pentafluoro-lambda6-sulphanyl)phenyl]acetic acidHCID 86614970Diisopropyl ether pentane

Product 1

HCID 896997003-(2-Amino-2-oxoethyl)-N-{2,4-dimethyl-5-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]-phenyl}-5-(pentafluoro-lambda6-sulphanyl)benzamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

85 mg (0.128 mmol) of the compound of Example 151 and 58 mg (0.154 mmol) of HATU were initially charged in 2 ml of DMF, and 67 μl (0.384 mmol) of N,N-diisopropylethylamine and 1.3 ml (0.640 mmol) of a 0.5 M solution of ammonia in THF were then added. After the reaction mixture had been stirred at RT for about 16 h, the entire mixture was separated into its components by preparative HPLC (Method 36). The product fractions were combined and concentrated to dryness on a rotary evaporator. For further purification, the product was triturated for 10 min at RT with a few ml of pentane/diisopropyl ether 4:1. The solid was separated off and dried under high vacuum. This gave 9 mg (11% of theory, 95% pure) of the title compound.

Workup

  1. customthe entire mixture was separated into its components by preparative HPLC (Method 36)
  2. concentrationconcentrated to dryness on a rotary evaporator
  3. customFor further purification
  4. customThe solid was separated off
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-a5fb340129ec441fb99f94e5b08e24cf
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

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