Sodium borohydride → HCID 25174896, compound

HRID 1526008Notes

Reaction equation

HRID 1526008 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:39]=[C:40]([F:42])[CH:41]=1)[C:5]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][N:11]=[C:10]2[NH:16][C:17](=[O:38])[C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]2)=[CH:20][C:19]=1[NH:31][CH:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1)=[O:6].[BH4-].[Na+]>C(O)(C)C>[F:1][C:2]1[CH:3]=[C:4]([CH:5]([OH:6])[C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][N:11]=[C:10]3[NH:16][C:17](=[O:38])[C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]3)=[CH:20][C:19]=2[NH:31][CH:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)[CH:39]=[C:40]([F:42])[CH:41]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 68670935HCID 68670935, compound

Product 1

HCID 25174896HCID 25174896, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of N-[5-(3,5-Difluoro-benzoyl)-1H-indazol-3-yl]-4-(4-methyl-piperazin-1-yl)-2-(tetrahydro-pyran-4-ylamino)-benzamide (130 mg, 0.226 mmol) and sodium borohydride (15 mg, 0.39 mmol) was dissolved at room temperature in i-propanol (20 mL). The reaction mixture was stirred for 4 hours, quenched with methanol and evaporated to dryness. Crude material was redissolved in DCM and washed with brine. After trituration with diethyl ether, 59 mg of the title compound were recovered (45% yield).

Workup

  1. customquenched with methanol
  2. customevaporated to dryness
  3. dissolutionCrude material was redissolved in DCM
  4. washwashed with brine
  5. customAfter trituration with diethyl ether, 59 mg of the title compound were recovered (45% yield)

Sources & evidence

ORD record
ord-24ceaea73f37423583d6baccc5777925
Source dataset
uspto-grants-2015_07
Patent number
US09085558B2

Reaction notes

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