Diisopropylamine → HCID 58733335, compound

HRID 16460Notes

Reaction equation

HRID 16460 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][CH2:10][C:11]([OH:13])=O)[CH:5]=[C:4]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]3[CH:27]=[CH:26][N:25]=[C:24]4[NH:28][CH:29]=[CH:30][C:23]=34)=[C:17]([F:31])[CH:16]=2)[N:3]=1.CN(C(ON1N=N[C:42]2[CH:43]=[CH:44][CH:45]=[N:46][C:41]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(NC(C)C)(C)C.N1CCCCC1>CN(C=O)C>[F:31][C:17]1[CH:16]=[C:15]([NH:14][C:4]2[CH:5]=[C:6]([CH2:8][CH2:9][CH2:10][C:11](=[O:13])[N:46]3[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45]3)[N:7]=[C:2]([NH2:1])[N:3]=2)[CH:20]=[CH:19][C:18]=1[O:21][C:22]1[CH:27]=[CH:26][N:25]=[C:24]2[NH:28][CH:29]=[CH:30][C:23]=12

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 8082PiperidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 587333374-(2-amino-6-{[3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]amino}pyrimidin-4-yl)butyric acid

Product 1

HCID 58733335HCID 58733335, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

70 mg (0.17 mmol) of 4-(2-amino-6-{[3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)phenyl]amino}pyrimidin-4-yl)butyric acid (from example 130) are dissolved in 2.0 ml of DMF, 60 mg (0.16 mmol) of HATU, 23 mg (0.17 mmol) of 1-hydroxy-1H-azobenzotriazole hydrate, 43 mg (0.33 mmol) of diisopropylamine and 28 mg (0.33 mmol) of piperidine are added and the mixture is stirred at RT for 20 hours. Volatile components are removed under reduced pressure and the product is purified by preparative HPLC. The resulting product is purified further by thick-layer chromatography (1 mm silica gel coating, mobile phase: DCM:methanol=9:1).

Workup

  1. customVolatile components are removed under reduced pressure
  2. customthe product is purified by preparative HPLC
  3. customThe resulting product is purified further by thick-layer chromatography (1 mm silica gel coating, mobile phase: DCM:methanol=9:1)

Sources & evidence

ORD record
ord-1aac5959433947cf9cd885997d839fa6
Source dataset
uspto-grants-2010_06
Patent number
US07737153B2

Reaction notes

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