Sodium Carbonate → HCID 135979591, compound

HRID 1783959Notes

Reaction equation

HRID 1783959 reaction equation
CN1CCN(C2C=CC(NC3C4[N:17]([N:29]=[CH:30]N=4)[C:18]([C:21]4C=C(C(N)=O)SC=4)=CN=3)=CC=2)CC1.Br[C:33]1[N:38]2[N:39]=[CH:40][N:41]=[C:37]2[C:36]([NH:42][C:43]2[CH:48]=[CH:47][C:46]([N:49]3[CH2:54][CH2:53][O:52][CH2:51][CH2:50]3)=[CH:45][C:44]=2[F:55])=[N:35][CH:34]=1.CC1(C)C(C)(C)OB(C2C=NNC=2)O1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:55][C:44]1[CH:45]=[C:46]([N:49]2[CH2:54][CH2:53][O:52][CH2:51][CH2:50]2)[CH:47]=[CH:48][C:43]=1[NH:42][C:36]1[C:37]2[N:38]([N:39]=[CH:40][N:41]=2)[C:33]([C:21]2[CH:30]=[N:29][NH:17][CH:18]=2)=[CH:34][N:35]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 575899284-{8-[4-(4-Methyl-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl}-thiophene-2-carboxylic acid amideHCID 57590026HCID 57590026, compound

Product 1

HCID 135979591HCID 135979591, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

This compound may be prepared using methods as described for Compound 6, step 4, using (5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-(2-fluoro-4-morpholin-4-yl-phenyl)-amine (80 mg, 0.203 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (79 mg, 0.406 mmol), and Pd(PPh3)4 (59 mg, 0.051 mmol) in 1.5N Na2CO3 (1.09 mL, 1.62 mmol) and dioxane (3.25 mL). The reaction mixture is purified by silica gel column chromatography eluting with 97:3 DCM:NH3 (7M in MeOH). The fractions containing the product are combined and evaporated in vacuo to afford a solid which is triturated with diethyl ether and petroleum ether to yield the title compound (29 mg, 38%). LCMS: Rt 2.90 min (96%).

Workup

  1. customThis compound may be prepared
  2. customThe reaction mixture is purified by silica gel column chromatography
  3. washeluting with 97:3 DCM
  4. additionThe fractions containing the product
  5. customevaporated in vacuo
  6. customto afford a solid which
  7. customis triturated with diethyl ether and petroleum ether

Sources & evidence

ORD record
ord-49a52185ac7d47708e965d2dad590b46
Source dataset
uspto-grants-2009_03
Patent number
US07501411B2

Reaction notes

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