Sodium borohydride → HCID 25174896, compound

HRID 512941Notes

Reaction equation

HRID 512941 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-8e4b14e5e55043a591a9b99845d593f9
Source dataset
uspto-grants-2015_08
Patent number
US09102662B2

Reaction notes

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